Product Name

  • Name

    BOC-(R)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID

  • EINECS 691-120-8
  • CAS No. 486460-00-8
  • Article Data61
  • CAS DataBase
  • Density 1.292 g/cm3
  • Solubility
  • Melting Point 136-138℃
  • Formula C15H18F3NO4
  • Boiling Point 443.1 °C at 760 mmHg
  • Molecular Weight 333.307
  • Flash Point 221.8 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 486460-00-8 (BOC-(R)-3-AMINO-4-(2,4,5-TRIFLUORO-PHENYL)-BUTYRIC ACID)
  • Hazard Symbols
  • Synonyms Benzenebutanoic acid, b-[[(1,1-dimethylethoxy)carbonyl]amino]-2,4,5-trifluoro-,(bR)-;(3R)-3-[(1,1-Dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoicacid;(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoicacid;(3R)-3-[N-(tert-Butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoicacid;(R)-3-(((tert-Butoxy)carbonyl)amino)-4-(2,4,5-trifluorophenyl)butyricacid;(R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid;
  • PSA 75.63000
  • LogP 3.40530

Synthetic route

3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester
881995-73-9

3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 3h;99%
With lithium hydroxide monohydrate; water In tetrahydrofuran for 16h;95.1%
Stage #1: 3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester With water; lithium hydroxide In methanol at 20℃; for 24h;
Stage #2: With hydrogenchloride In water; ethyl acetate		95%
C15H16F3NO4

C15H16F3NO4

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
With palladium on carbon; hydrogen In methanol for 24h;99%
(R)-tert-butyl (4-hydroxy-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate
1048703-14-5

(R)-tert-butyl (4-hydroxy-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
With sodium hypochlorite; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water; acetonitrile at 38℃; for 0.333333h; Solvent;98%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In dichloromethane at 0℃; for 2h;90%
Stage #1: (R)-tert-butyl (4-hydroxy-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In dichloromethane at 0℃; for 2h;
Stage #2: With hydrogenchloride In dichloromethane; water pH=2 - 3;		90%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical90%
(R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester
1152439-74-1

(R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate In methanol; water at 30 - 40℃;95%
Stage #1: (R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester With water; sodium hydroxide In methanol at 40 - 45℃; for 2h;
Stage #2: In methanol; water pH=3; Acidic conditions;
Stage #1: (R)-3-tertbutoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester With sodium hydroxide In methanol; water at 40 - 45℃; for 2h;
Stage #2: In methanol; water pH=3;
[3-diazo-2-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester
486460-25-7

[3-diazo-2-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
With silver benzoate In 1,4-dioxane; water for 1.5h; Sonication;94%
With silver benzoate In 1,4-dioxane at 20℃; for 2h; sonication;401 mg
With silver benzoate In 1,4-dioxane; water for 2h; Sonographic reaction;
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid
936630-57-8

(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 20℃;91%
Stage #1: (R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid With lithium hydroxide In 1,4-dioxane; water at 0 - 30℃;
Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 25 - 30℃;		91%
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 24h;91%
(R)-cyclohexyl 3-(tert-butoxycarbonyl amino)-4-(2,4,5-trifluorophenyl)butyrate
1276113-61-1

(R)-cyclohexyl 3-(tert-butoxycarbonyl amino)-4-(2,4,5-trifluorophenyl)butyrate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Stage #1: (R)-cyclohexyl 3-(tert-butoxycarbonyl amino)-4-(2,4,5-trifluorophenyl)butyrate With water; potassium carbonate at 60℃; for 3h;
Stage #2: With hydrogenchloride; water at 20 - 30℃; for 2h;		90%
Stage #1: (R)-cyclohexyl 3-(tert-butoxycarbonyl amino)-4-(2,4,5-trifluorophenyl)butyrate With potassium carbonate In water at 60℃; for 3h;
Stage #2: With hydrogenchloride In water at 20 - 30℃; for 2h;		90%
C16H20F3NO2

C16H20F3NO2

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
With potassium permanganate In acetone at 20℃; for 3h; Concentration;89%
With ruthenium trichloride; sodium periodate In water; acetonitrile at -10℃; for 2h;70%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(R)-3-((R)-1-phenylethylamino)-4-(2,4,5-trifluorophenyl)-N-phenyl butanamide

(R)-3-((R)-1-phenylethylamino)-4-(2,4,5-trifluorophenyl)-N-phenyl butanamide

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Stage #1: (R)-3-((R)-1-phenylethylamino)-4-(2,4,5-trifluorophenyl)-N-phenyl butanamide With 5%-palladium/activated carbon; hydrogen In methanol at 70℃; under 6000.6 Torr;
Stage #2: With hydrogenchloride; water In methanol at 90℃;
Stage #3: di-tert-butyl dicarbonate In tetrahydrofuran; water at 10 - 20℃; for 20h;		88%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

diethyl 2-((R)-1-((R)-1,1-dimethylethylsulfinamido)-2-(2,4,5-trifluorophenyl)ethyl)malonate

diethyl 2-((R)-1-((R)-1,1-dimethylethylsulfinamido)-2-(2,4,5-trifluorophenyl)ethyl)malonate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Stage #1: diethyl 2-((R)-1-((R)-1,1-dimethylethylsulfinamido)-2-(2,4,5-trifluorophenyl)ethyl)malonate With hydrogenchloride In water for 18h; Reflux;
Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In water at 20℃; pH=8;		88%
(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester
881995-69-3

(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Stage #1: (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester; di-tert-butyl dicarbonate With triethylamine In ethyl acetate at 20 - 30℃; for 7h;
Stage #2: With water; sodium hydroxide In ethanol at 20 - 30℃; for 2h;		85.5%
Stage #1: (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester With water; lithium hydroxide In tetrahydrofuran at 0 - 30℃;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 25 - 30℃; for 6h;
Stage #3: With sodium hydrogen sulfate In water pH=2;		80%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

di-tert-butyl 2-((R)-1-((R)-1,1-dimethylethylsulfinamido)-2-(2,4,5-trifluorophenyl)ethyl)malonate

di-tert-butyl 2-((R)-1-((R)-1,1-dimethylethylsulfinamido)-2-(2,4,5-trifluorophenyl)ethyl)malonate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Stage #1: di-tert-butyl 2-((R)-1-((R)-1,1-dimethylethylsulfinamido)-2-(2,4,5-trifluorophenyl)ethyl)malonate With hydrogenchloride In water for 9h; Reflux;
Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In water at 20℃;		83%
(R)-tert-butyl (1-cyano-3-(2,4,5-trifluorophenyl)propan-2-yl)carbamate
1246960-23-5

(R)-tert-butyl (1-cyano-3-(2,4,5-trifluorophenyl)propan-2-yl)carbamate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 75 - 85℃;81%
With dihydrogen peroxide; sodium hydroxide In water at 100℃; for 3h;75%
Stage #1: (R)-tert-butyl (1-cyano-3-(2,4,5-trifluorophenyl)propan-2-yl)carbamate With potassium hydroxide In ethanol; water at 80℃; for 12h;
Stage #2: With oxalic acid In ethanol; water at 20℃;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

C19H16F3NO5

C19H16F3NO5

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Stage #1: C19H16F3NO5 With hydrogenchloride; palladium on activated charcoal; hydrogen In diethyl ether; ethanol at 20℃; for 10h;
Stage #2: With hydrogenchloride In diethyl ether; ethanol for 0.5h; Reflux;
Stage #3: di-tert-butyl dicarbonate With lithium hydroxide In tetrahydrofuran; diethyl ether; ethanol at 20℃; for 8h;		66%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-hydroxyethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate

2-hydroxyethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Stage #1: 2-hydroxyethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate With pyridoxal 5'-phosphate; recombinant aminotransferase from Arthobacter sp.; water; isopropylamine In dimethyl sulfoxide at 45℃; for 24h; Green chemistry; Enzymatic reaction;
Stage #2: With lithium hydroxide In dimethyl sulfoxide at 45℃; for 3h; Green chemistry;
Stage #3: di-tert-butyl dicarbonate In tetrahydrofuran; dimethyl sulfoxide at 35℃; Green chemistry; enantioselective reaction;		60.6%
C11H10F3NO3

C11H10F3NO3

tert-butyl alcohol
75-65-0

tert-butyl alcohol

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
With bromine; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 50℃; Hofmann Rearrangement; enantioselective reaction;55%
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
769195-26-8

4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / ammonium acetate / methanol / 7 h / Heating
2: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr
3: 93 percent / CH2Cl2 / 3 h / 20 °C
4: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: ammonium acetate / methanol / 60 - 63 °C
2.1: sulfuric acid / methanol / -10 - 0 °C
2.2: 2 h / -10 - 0 °C
2.3: pH 8 - 9
3.1: isopropyl alcohol / 3 h / 25 - 30 °C
4.1: sodium carbonate / water / pH 8 - 9
5.1: water; lithium hydroxide / tetrahydrofuran / 0 - 30 °C
6.1: water; tetrahydrofuran / 6 h / 25 - 30 °C
6.2: pH 2
View Scheme
Multi-step reaction with 4 steps
1: acetic acid / methanol / Reflux; Large scale
2: boron trifluoride diethyl etherate; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / -78 - 0 °C / Large scale
3: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 25 °C
4: lithium hydroxide monohydrate / methanol; water / 30 - 40 °C
View Scheme
(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester
881995-69-3

(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / CH2Cl2 / 3 h / 20 °C
2: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: water; lithium hydroxide / tetrahydrofuran / 0 - 30 °C
2.1: water; tetrahydrofuran / 6 h / 25 - 30 °C
2.2: pH 2
View Scheme
methyl 3-amino-4-(2,4,5-trifluorophenyl)but-2-enoate

methyl 3-amino-4-(2,4,5-trifluorophenyl)but-2-enoate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr
2: 93 percent / CH2Cl2 / 3 h / 20 °C
3: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C
View Scheme
(2,4,5-trifluorophenyl)acetic acid
209995-38-0

(2,4,5-trifluorophenyl)acetic acid

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 95 percent / N,N-dimethylaminopyridine; N,N-diisopropylethylamine; trimethylacetylchloride / acetonitrile / 3 h / 45 °C
2: 88.7 percent / toluene / 3 h / Heating
3: 95 percent / ammonium acetate / methanol / 7 h / Heating
4: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr
5: 93 percent / CH2Cl2 / 3 h / 20 °C
6: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 3 h / 50 °C
2.1: ethanol / 3 h / 70 °C
3.1: formic acid / ethanol / 3 h / Reflux
3.2: 2 h / 40 °C / Reflux
4.1: methanol / Reflux
5.1: sodium carbonate / water; methanol / 3 h / 30 °C / pH 10
6.1: sodium hydroxide; water / methanol / 2 h / 40 - 45 °C
6.2: pH 3 / Acidic conditions
View Scheme
Multi-step reaction with 8 steps
1.1: 1,1'-carbonyldiimidazole
1.2: 3 h / 50 °C
2.1: 3 h / 70 °C
3.1: ethanol / 3 h / Reflux
4.1: ethanol; sodium cyanoborohydride / 2 h / 40 °C / Reflux
5.1: methanol / Reflux
6.1: Basic conditions
7.1: sodium carbonate / water; methanol / 3 h / 30 °C / pH 10
8.1: sodium hydroxide / water; methanol / 2 h / 40 - 45 °C
8.2: pH 3
View Scheme
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
764667-64-3

5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 88.7 percent / toluene / 3 h / Heating
2: 95 percent / ammonium acetate / methanol / 7 h / Heating
3: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr
4: 93 percent / CH2Cl2 / 3 h / 20 °C
5: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 60 - 63 °C
2.1: ammonium acetate / methanol / 60 - 63 °C
3.1: sulfuric acid / methanol / -10 - 0 °C
3.2: 2 h / -10 - 0 °C
3.3: pH 8 - 9
4.1: isopropyl alcohol / 3 h / 25 - 30 °C
5.1: sodium carbonate / water / pH 8 - 9
6.1: water; lithium hydroxide / tetrahydrofuran / 0 - 30 °C
7.1: water; tetrahydrofuran / 6 h / 25 - 30 °C
7.2: pH 2
View Scheme
Multi-step reaction with 3 steps
1.1: acetonitrile / 24 h / 80 - 84 °C / Inert atmosphere
2.1: salicylic acid; ammonium acetate; Ru(OAc)2((R)-dm-Segphos); hydrogen / 20 h / 40 - 80 °C / Green chemistry
3.1: triethylamine / ethyl acetate / 7 h / 20 - 30 °C
3.2: 2 h / 20 - 30 °C
View Scheme
Multi-step reaction with 7 steps
1.1: toluene / Reflux
2.1: ammonium acetate / acetonitrile / Reflux
3.1: N-tert-butylaminoborane / tetrahydrofuran / 20 °C
3.2: 8 h / 0 - 20 °C
4.1: acetonitrile; water / 0.5 h / Reflux
5.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h
6.1: palladium on activated charcoal; hydrogen / methanol / 25 - 30 °C
7.1: sodium carbonate / tetrahydrofuran; water / 25 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1: acetonitrile / 65 °C
2: sodium tetrahydroborate; ethanol / 65 °C / Cooling with ice
3: hydrogenchloride / methanol / 20 °C / pH 1
4: sodium hydrogencarbonate / tetrahydrofuran; water / 24 h / 20 °C
View Scheme
methyl (3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoate (1S)-(+)-10-camphorsulfonic acid

methyl (3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoate (1S)-(+)-10-camphorsulfonic acid

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiOH*H2O / tetrahydrofuran; H2O / 24 h
2: 14 g / LiOH*H2O / tetrahydrofuran; H2O / 12 h / 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1.) NaH; 2.) SOCl2

1.) NaH; 2.) SOCl2

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: aq. HCl / acetonitrile / 72 h / 20 °C
1.2: 2.41 g / triethylamine / CH2Cl2 / 16 h / 20 °C
2.1: aq. LiOH / tetrahydrofuran / 20 °C
3.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C
3.2: 0.36 g / diethyl ether / 1 h
4.1: 401 mg / aq. silver benzoate / dioxane / 2 h / 20 °C / sonication
View Scheme
2,4,5-trifluorobenzyl bromide
157911-56-3

2,4,5-trifluorobenzyl bromide

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-BuLi / tetrahydrofuran / -78 °C
1.2: tetrahydrofuran / -78 °C
2.1: aq. HCl / acetonitrile / 72 h / 20 °C
2.2: 2.41 g / triethylamine / CH2Cl2 / 16 h / 20 °C
3.1: aq. LiOH / tetrahydrofuran / 20 °C
4.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C
4.2: 0.36 g / diethyl ether / 1 h
5.1: 401 mg / aq. silver benzoate / dioxane / 2 h / 20 °C / sonication
View Scheme
(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2,4,5-trifluorophenyl)propanoate
486460-08-6

(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2,4,5-trifluorophenyl)propanoate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: aq. LiOH / tetrahydrofuran / 20 °C
2.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C
2.2: 0.36 g / diethyl ether / 1 h
3.1: 401 mg / aq. silver benzoate / dioxane / 2 h / 20 °C / sonication
View Scheme
(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2',4',5'-trifluorobenzyl)-pyrazine
486460-07-5

(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2',4',5'-trifluorobenzyl)-pyrazine

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: aq. HCl / acetonitrile / 72 h / 20 °C
1.2: 2.41 g / triethylamine / CH2Cl2 / 16 h / 20 °C
2.1: aq. LiOH / tetrahydrofuran / 20 °C
3.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C
3.2: 0.36 g / diethyl ether / 1 h
4.1: 401 mg / aq. silver benzoate / dioxane / 2 h / 20 °C / sonication
View Scheme
(R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid
486460-09-7

(R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C
1.2: 0.36 g / diethyl ether / 1 h
2.1: 401 mg / aq. silver benzoate / dioxane / 2 h / 20 °C / sonication
View Scheme
Multi-step reaction with 2 steps
1.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C
1.2: 1 h / -20 °C
2.1: silver benzoate / water; 1,4-dioxane / 1.5 h / Sonication
View Scheme
Multi-step reaction with 2 steps
1.1: isobutyl chloroformate; triethylamine / diethyl ether / 0.25 h / -20 °C
1.2: 1 h / -20 °C
2.1: silver benzoate / 1,4-dioxane; water / 2 h
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid hydrochloride
1204818-19-8

(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid hydrochloride

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran at 0 - 20℃;
3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyric acid ethyl ester

3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyric acid ethyl ester

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

Conditions
ConditionsYield
Stage #1: 3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyric acid ethyl ester With water; sodium hydroxide In methanol at 40 - 45℃;
Stage #2: With hydrogenchloride In water pH=2 - 3; Cooling with ice;
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
762240-92-6

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate
486460-23-5

(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 55 - 60℃; for 12h;99.02%
With triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 20 - 50℃; Reagent/catalyst; Solvent;96%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 0 - 20℃; for 24h;95%
3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine
486460-21-3

3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate
486460-23-5

(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate

Conditions
ConditionsYield
With (2-iodo-5-methoxyphenyl)boronic acid; 4-(dimethylamino)pyridine N-oxide In fluorobenzene for 40h; Catalytic behavior; Reagent/catalyst;99%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In water; ethyl acetate at 20℃; for 12h;91%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;88%
C11H13F5N4

C11H13F5N4

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

tert-butyl ((2R)-4-oxo-4-(1-(perfluoroethyl)-4,5,5a,8,9,9a-hexahydro-[1,2,4]triazolo[4,3-a][1,6]naphthyridin-7(6H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate

tert-butyl ((2R)-4-oxo-4-(1-(perfluoroethyl)-4,5,5a,8,9,9a-hexahydro-[1,2,4]triazolo[4,3-a][1,6]naphthyridin-7(6H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;98%
rac-(5aS,9aR)-1-(6-ethoxypyridin-2-yl)-4,5,5a,6,7,8,9,9a-octahydro[1,2,4]triazolo[4,3-a][1,6]naphthyridine

rac-(5aS,9aR)-1-(6-ethoxypyridin-2-yl)-4,5,5a,6,7,8,9,9a-octahydro[1,2,4]triazolo[4,3-a][1,6]naphthyridine

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

tert-butyl ((R)-4-((5aS*,9aR*)-1-(6-ethoxypyridin-2-yl)-4,5,5a,8,9,9a-hexahydro-[1,2,4]triazolo[4,3-a][1,6]naphthyridin-7(6H)-yl)-4-oxo-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate

tert-butyl ((R)-4-((5aS*,9aR*)-1-(6-ethoxypyridin-2-yl)-4,5,5a,8,9,9a-hexahydro-[1,2,4]triazolo[4,3-a][1,6]naphthyridin-7(6H)-yl)-4-oxo-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;98%
hexahydro-2-(4-cyanophenyl)-imidazo[1,5-a]pyrazin-3-one
1256815-22-1

hexahydro-2-(4-cyanophenyl)-imidazo[1,5-a]pyrazin-3-one

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

tert-butyl [(1R)-3-[2-(4-cyanophenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate
1256815-41-4

tert-butyl [(1R)-3-[2-(4-cyanophenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;97%
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
762240-92-6

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

Sitagliptin hydrochloride

Sitagliptin hydrochloride

Conditions
ConditionsYield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid; 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride In N,N-dimethyl-formamide for 0.166667h;
Stage #2: With 2-chloro-1,3-dimethylimidazolinium chloride In N,N-dimethyl-formamide at 20 - 25℃; for 5h; Reagent/catalyst;		97%
1-(1-methanesulfonylpiperazin-2-yl)cyclopropylcarboxylic acid methyl ester

1-(1-methanesulfonylpiperazin-2-yl)cyclopropylcarboxylic acid methyl ester

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

1-[4-[(3R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoyl]-1-methanesulfonylpiperazin-2-yl]cyclopropylcarboxylic acid methyl ester

1-[4-[(3R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoyl]-1-methanesulfonylpiperazin-2-yl]cyclopropylcarboxylic acid methyl ester

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 0 - 30℃; for 1h; Inert atmosphere;97%
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
762240-92-6

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

sitagliptin
486460-32-6

sitagliptin

Conditions
ConditionsYield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With triethylamine In dichloromethane for 0.166667h;
Stage #2: With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 25 - 30℃; for 4h;
Stage #3: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride Further stages;		96.5%
hexahydro-2-(pyridin-2-yl)-imidazo[1,5-a]pyrazin-3(5h)-one
1256815-18-5

hexahydro-2-(pyridin-2-yl)-imidazo[1,5-a]pyrazin-3(5h)-one

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

tert-butyl [(1R)-3-[2-(pyridin-2-yl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate
1256815-36-7

tert-butyl [(1R)-3-[2-(pyridin-2-yl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;96%
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

sitagliptin
486460-32-6

sitagliptin

Conditions
ConditionsYield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With thionyl chloride In ethyl acetate at 26℃; for 2h;
Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride With triethylamine In ethyl acetate at 25℃; Solvent; Temperature;		96%
Stage #1: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride; (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With 1-methyl-1H-imidazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0 - 20℃; for 16h;
Stage #2: With hydrogenchloride In ethanol at 20℃; for 18h;
Stage #3: With sodium hydroxide In ethanol; water pH=10 - 12; Time; Solvent;		90%
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With pivaloyl chloride; sodium carbonate In toluene Cooling;
Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride In toluene
Stage #3: With hydrogenchloride In water; toluene Reagent/catalyst;		4.4 g
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

(R)-3-(amino-d2)-4-(2,4,5-trifluorophenyl)-2,2-d2-butanoic acid deuterochloride
1078568-89-4

(R)-3-(amino-d2)-4-(2,4,5-trifluorophenyl)-2,2-d2-butanoic acid deuterochloride

Conditions
ConditionsYield
With water-d2; hydrogen chloride at 70 - 160℃; for 15h;95%
hexahydro-2-(3-cyanobenzyl)-imidazo[1,5-a]pyrazin-3-one
1256815-17-4

hexahydro-2-(3-cyanobenzyl)-imidazo[1,5-a]pyrazin-3-one

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

tert-butyl [(1R)-3-[2-(3-cyanobenzyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate

tert-butyl [(1R)-3-[2-(3-cyanobenzyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;95%
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate
486460-23-5

(R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate

Conditions
ConditionsYield
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0 - 20℃; for 16h;95%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 0 - 20℃; for 24h;95%
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With Triisopropyl borate; sulfuric acid In toluene at 20℃; for 2h; Reflux;
Stage #2: 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride With triethylamine In toluene at 80℃; Reagent/catalyst; Temperature; Solvent; Concentration; Reflux; Dean-Stark;		92.1%
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-α]pyrazine hydrochloride

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

N-Boc-sitagliptin

N-Boc-sitagliptin

Conditions
ConditionsYield
With 4-(dimethylamino)pyridine N-oxide; sodium hydroxide; 2,6-difluorophenylboronic acid In fluorobenzene; water at 100℃; for 23h; Reagent/catalyst; Molecular sieve;95%
C14H19N3O2
1256815-14-1

C14H19N3O2

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

tert-butyl [(1R)-3-[2-(2-methoxybenzyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate
1256815-32-3

tert-butyl [(1R)-3-[2-(2-methoxybenzyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;94%
4-[3-methyl-5-(trifluoromethyl)-4H-1,2,4-triazol-4-yl]piperidine
868669-70-9

4-[3-methyl-5-(trifluoromethyl)-4H-1,2,4-triazol-4-yl]piperidine

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

tert-butyl (R)-(4-(4-(3-methyl-5-(trifluoromethyl)-4H-1,2,4-triazol-4-yl)piperidin-1-yl)-4-oxo-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate

tert-butyl (R)-(4-(4-(3-methyl-5-(trifluoromethyl)-4H-1,2,4-triazol-4-yl)piperidin-1-yl)-4-oxo-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;93%
bis(pentafluorophenyl)carbonate
59483-84-0

bis(pentafluorophenyl)carbonate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

(R)-pentafluorophenyl 3-(t-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoate

(R)-pentafluorophenyl 3-(t-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoate

Conditions
ConditionsYield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With triethylamine In N,N-dimethyl-formamide at 25℃; for 0.333333h;
Stage #2: bis(pentafluorophenyl)carbonate In N,N-dimethyl-formamide at 25℃; for 2h;		92.3%
hexahydro-2-(4-chlorobenzyl)-imidazo[1,5-a]pyrazin-3-one
1256815-12-9

hexahydro-2-(4-chlorobenzyl)-imidazo[1,5-a]pyrazin-3-one

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

tert-butyl [(1R)-3-[2-(4-chlorobenzyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate
1256815-30-1

tert-butyl [(1R)-3-[2-(4-chlorobenzyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazin-7(8H)-yl]-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;92%
7-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-one hydrochloride
1364122-94-0

7-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-one hydrochloride

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

(R)-[3-(7-methoxy-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-yl)-3-oxo-1-(2,4,5-trifluorophenyl)propyl]carbamic acid tert-butyl ester

(R)-[3-(7-methoxy-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-yl)-3-oxo-1-(2,4,5-trifluorophenyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole In acetonitrile at 20℃; for 0.5h;
Stage #2: 7-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-one hydrochloride In acetonitrile at 65 - 70℃; for 22h;		92%
bis-(p-nitrophenyl) carbonate
5070-13-3

bis-(p-nitrophenyl) carbonate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

(R)-4-nitrophenyl 3-(t-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoate

(R)-4-nitrophenyl 3-(t-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoate

Conditions
ConditionsYield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With triethylamine In N,N-dimethyl-formamide at 25℃; for 0.333333h;
Stage #2: bis-(p-nitrophenyl) carbonate In N,N-dimethyl-formamide at 25 - 70℃; for 4h;		91.9%
2,2'-dipyridyl carbonate
1659-31-0

2,2'-dipyridyl carbonate

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

(R)-pyridin-2-yl 3-(t-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoate

(R)-pyridin-2-yl 3-(t-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoate

Conditions
ConditionsYield
Stage #1: (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid With triethylamine In N,N-dimethyl-formamide at 25℃; for 0.333333h;
Stage #2: 2,2'-dipyridyl carbonate In N,N-dimethyl-formamide at 25 - 70℃; for 2h;		91.4%
C10H13F3N4

C10H13F3N4

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

tert-butyl ((2R)-4-oxo-4-(1-(trifluoromethyl)-4,5,5a,8,9,9a-hexahydro-[1,2,4]triazolo[4,3-a][1,6]naphthyridin-7(6H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate

tert-butyl ((2R)-4-oxo-4-(1-(trifluoromethyl)-4,5,5a,8,9,9a-hexahydro-[1,2,4]triazolo[4,3-a][1,6]naphthyridin-7(6H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;91%
1,2-diazepane dihydrochloride

1,2-diazepane dihydrochloride

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

(R)-[3-[1,2]diazepan-1-yl-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester
939964-18-8

(R)-[3-[1,2]diazepan-1-yl-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;90%

Boc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid Specification

The Boc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid, with the CAS registry number 486460-00-8, is also known as (3R)-N-(tert-Butoxycarbonyl)-3-amino-4-(2,4,5-trifluorophenyl)butanoic acid. It belongs to the product categories of Organic matters.This chemical's molecular formula is C15H18F3NO4 and molecular weight is 333.30. What's more,Its systematic name is (3R)-3-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-(2,4,5-trifluorophenyl)butanoic acid.

Physical properties about Boc-(R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic acid are:(1)ACD/LogP: 2.341; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.98; (4)ACD/LogD (pH 7.4): -0.78; (5)ACD/BCF (pH 5.5): 1.55; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 19.59; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.494; (13)Molar Refractivity: 75.072 cm3; (14)Molar Volume: 257.776 cm3; (15)Surface Tension: 40.6020011901855 dyne/cm; (16)Density: 1.293 g/cm3; (17)Flash Point: 221.754 °C; (18)Enthalpy of Vaporization: 73.842 kJ/mol; (19)Boiling Point: 443.058 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:Fc1cc(c(F)cc1F)C[C@@H](NC(=O)OC(C)(C)C)CC(=O)O;
(2)Std. InChI:InChI=1S/C15H18F3NO4/c1-15(2,3)23-14(22)19-9(6-13(20)21)4-8-5-11(17)12(18)7-10(8)16/h5,7,9H,4,6H2,1-3H3,(H,19,22)(H,20,21)/t9-/m1/s1;
(3)Std. InChIKey:TUAXCHGULMWHIO-SECBINFHSA-N.

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