(R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid supplier

Name
(R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid
EINECS 1308068-626-2
CAS No. 936630-57-8
Article Data19
CAS DataBase
Density 1.399 g/cm³
Solubility
Melting Point 217-219 °C(Solv: water (7732-18-5); acetone (67-64-1))
Formula C₁₀H₁₀F₃NO₂
Boiling Point 326.6 °C at 760 mmHg
Molecular Weight 233.19
Flash Point 151.3 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms I01-7533
PSA 63.32000
LogP 2.14870

Synthetic route

: C35H27Cl3F3N3NiO3

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: 1644308-43-9
(R)-N-(2-benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)methyl]-2-pyrrolidinecarboxamide

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 50℃;	A 85% B 96%

: 1402570-02-8
(R)-3-benzoylamino-4-(2,4,5-trifluorophenyl)butanoic acid methyl ester

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In water Reflux;	95%

: 1334630-72-6
(S)-methyl 3-(dibenzylamino)-4-oxo-4-(2,4,5-trifluorophenyl)butanoate

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Stage #1: (S)-methyl 3-(dibenzylamino)-4-oxo-4-(2,4,5-trifluorophenyl)butanoate With palladium 10% on activated carbon; hydrogen In ethanol at 25℃; for 5h; Stage #2: With hydrogenchloride; water pH=5 - 6;	93.2%

: 1151240-91-3
(3R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In water at 27℃; for 6h; Reflux;	92%
With lithium hydroxide pH=> 10;

: 767352-29-4
(R)-3-((benzyloxy)amino)-4-(2,4,5-trifluorophenyl)butanoic acid

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2068.65 Torr; for 12h;	91%

: C18H22F3NO5S

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 20℃; pH=1;	91%

: 868125-58-0
methyl (R)-3-(benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoate

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Stage #1: methyl N-benzyloxy-4-(2,4,5-trifluorophenyl)-3(R)-aminobutanoate With palladium on activated charcoal In chloroform for 6h; Autoclave; Stage #2: With hydrogenchloride In water for 6h; pH=4; Reflux;	77%

: 1151240-92-4
ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: 1151240-90-2
(S)-ethyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate

Conditions

Conditions	Yield
With Burkholderia cepacia lipase; water In di-isopropyl ether at 45℃; for 120h; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;	A 43% B n/a

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

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water for 24h;

: 1253056-05-1
(S)-1-(2,4,5-trifluorophenyl)pent-4-en-2-amine

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
With sodium periodate; rhodium(III) chloride hydrate In acetonitrile at 12 - 20℃; for 2h;

: 1246961-45-4
(R)-t-butyl 3-(t-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoate

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 6h;

: 502462-00-2
(2,4,5-trifluorophenyl)-magnesium bromide

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 2 h / 25 °C / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 25 °C 2.2: pH 5 - 6 View Scheme

: 327-52-6
1-bromo-2,4,5-trifluorobenzene

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 3 h / 25 °C / Inert atmosphere 2.1: 2 h / 25 °C / Inert atmosphere 3.1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 25 °C 3.2: pH 5 - 6 View Scheme

: 165047-24-5
2,4,5-trifluorobenzaldehyde

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium hydroxide; water / methanol; water / 0.5 h / Cooling with ice 2.1: sodium tetrahydroborate; isopropyl alcohol / chloroform / 0.5 h / 27 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C 4.1: iodine / 27 °C 5.1: basic alumina / dichloromethane / 2 h / 27 °C 6.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 6.2: polymethylhydrosiloxane (PMHS) / 17 h 6.3: 1 h 7.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme
Multi-step reaction with 8 steps 1.1: sodium hydroxide; water / methanol; water / 0.5 h / Cooling with ice 2.1: sodium tetrahydroborate; isopropyl alcohol / chloroform / 0.5 h / 27 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C 4.1: iodine / 27 °C 5.1: basic alumina / dichloromethane / 2 h / 27 °C 6.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 6.2: polymethylhydrosiloxane (PMHS) / 17 h 6.3: 1 h 7.1: hydrogen / ethyl acetate / 5 h / 27 °C / 2585.81 Torr 8.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme

Yield

Multi-step reaction with 7 steps
1.1: sodium hydroxide; water / methanol; water / 0.5 h / Cooling with ice
2.1: sodium tetrahydroborate; isopropyl alcohol / chloroform / 0.5 h / 27 °C
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C
4.1: iodine / 27 °C
5.1: basic alumina / dichloromethane / 2 h / 27 °C
6.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h
6.2: polymethylhydrosiloxane (PMHS) / 17 h
6.3: 1 h
7.1: hydrogenchloride / water / 6 h / 27 °C / Reflux
View Scheme

Multi-step reaction with 8 steps
1.1: sodium hydroxide; water / methanol; water / 0.5 h / Cooling with ice
2.1: sodium tetrahydroborate; isopropyl alcohol / chloroform / 0.5 h / 27 °C
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C
4.1: iodine / 27 °C
5.1: basic alumina / dichloromethane / 2 h / 27 °C
6.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h
6.2: polymethylhydrosiloxane (PMHS) / 17 h
6.3: 1 h
7.1: hydrogen / ethyl acetate / 5 h / 27 °C / 2585.81 Torr
8.1: hydrogenchloride / water / 6 h / 27 °C / Reflux
View Scheme

: 3-(2,4,5-trifluorophenyl)nitroethane

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C 2.1: iodine / 27 °C 3.1: basic alumina / dichloromethane / 2 h / 27 °C 4.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 4.2: polymethylhydrosiloxane (PMHS) / 17 h 4.3: 1 h 5.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme
Multi-step reaction with 6 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C 2.1: iodine / 27 °C 3.1: basic alumina / dichloromethane / 2 h / 27 °C 4.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 4.2: polymethylhydrosiloxane (PMHS) / 17 h 4.3: 1 h 5.1: hydrogen / ethyl acetate / 5 h / 27 °C / 2585.81 Torr 6.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C
2.1: iodine / 27 °C
3.1: basic alumina / dichloromethane / 2 h / 27 °C
4.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h
4.2: polymethylhydrosiloxane (PMHS) / 17 h
4.3: 1 h
5.1: hydrogenchloride / water / 6 h / 27 °C / Reflux
View Scheme

Multi-step reaction with 6 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C
2.1: iodine / 27 °C
3.1: basic alumina / dichloromethane / 2 h / 27 °C
4.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h
4.2: polymethylhydrosiloxane (PMHS) / 17 h
4.3: 1 h
5.1: hydrogen / ethyl acetate / 5 h / 27 °C / 2585.81 Torr
6.1: hydrogenchloride / water / 6 h / 27 °C / Reflux
View Scheme

: 913623-45-7
1,2,4-trifluoro-5-(2-nitrovinyl)-benzene

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: sodium tetrahydroborate; isopropyl alcohol / chloroform / 0.5 h / 27 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C 3.1: iodine / 27 °C 4.1: basic alumina / dichloromethane / 2 h / 27 °C 5.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 5.2: polymethylhydrosiloxane (PMHS) / 17 h 5.3: 1 h 6.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate; isopropyl alcohol / chloroform / 0.5 h / 27 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C 3.1: iodine / 27 °C 4.1: basic alumina / dichloromethane / 2 h / 27 °C 5.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 5.2: polymethylhydrosiloxane (PMHS) / 17 h 5.3: 1 h 6.1: hydrogen / ethyl acetate / 5 h / 27 °C / 2585.81 Torr 7.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1.1: sodium tetrahydroborate; isopropyl alcohol / chloroform / 0.5 h / 27 °C
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C
3.1: iodine / 27 °C
4.1: basic alumina / dichloromethane / 2 h / 27 °C
5.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h
5.2: polymethylhydrosiloxane (PMHS) / 17 h
5.3: 1 h
6.1: hydrogenchloride / water / 6 h / 27 °C / Reflux
View Scheme

Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate; isopropyl alcohol / chloroform / 0.5 h / 27 °C
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 27 °C
3.1: iodine / 27 °C
4.1: basic alumina / dichloromethane / 2 h / 27 °C
5.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h
5.2: polymethylhydrosiloxane (PMHS) / 17 h
5.3: 1 h
6.1: hydrogen / ethyl acetate / 5 h / 27 °C / 2585.81 Torr
7.1: hydrogenchloride / water / 6 h / 27 °C / Reflux
View Scheme

: 2-hydroxy-3-nitro-4-(2,4,5-trifluoro-phenyl)butyric acid ethyl ester

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: iodine / 27 °C 2.1: basic alumina / dichloromethane / 2 h / 27 °C 3.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 3.2: polymethylhydrosiloxane (PMHS) / 17 h 3.3: 1 h 4.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: iodine / 27 °C 2.1: basic alumina / dichloromethane / 2 h / 27 °C 3.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 3.2: polymethylhydrosiloxane (PMHS) / 17 h 3.3: 1 h 4.1: hydrogen / ethyl acetate / 5 h / 27 °C / 2585.81 Torr 5.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme

: 2-acetoxy-3-nitro-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: basic alumina / dichloromethane / 2 h / 27 °C 2.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 2.2: polymethylhydrosiloxane (PMHS) / 17 h 2.3: 1 h 3.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: basic alumina / dichloromethane / 2 h / 27 °C 2.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 2.2: polymethylhydrosiloxane (PMHS) / 17 h 2.3: 1 h 3.1: hydrogen / ethyl acetate / 5 h / 27 °C / 2585.81 Torr 4.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme

: 3-nitro-4-(2,4,5-trifluorophenyl)but-2-enoic acid ethyl ester

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: copper (II)-fluoride; 2-(diphenylphosphino)ferrocenylethyldicyclohexylphosphine / toluene / 1 h 1.2: polymethylhydrosiloxane (PMHS) / 17 h 1.3: 1 h 2.1: hydrogen / ethyl acetate / 5 h / 27 °C / 2585.81 Torr 3.1: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme

: 3-nitro-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / ethyl acetate / 5 h / 27 °C / 2585.81 Torr 2: hydrogenchloride / water / 6 h / 27 °C / Reflux View Scheme

: 1151240-88-8
3-oxo-4-(2,4,5-trifluorophenyl)-butyric acid ethyl ester

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: 1151240-91-3
(3R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester

Conditions

Conditions	Yield
With pyridoxal 5'-phosphate; recombinant aminotransferase from Arthobacter sp.; water; isopropylamine In dimethyl sulfoxide at 45℃; for 8h; pH=8.5; Catalytic behavior; Concentration; Time; Enzymatic reaction; Overall yield = 95.87 %Chromat.; enantioselective reaction;	A 34.48 %Chromat. B n/a

: 209995-38-0
(2,4,5-trifluorophenyl)acetic acid

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid propyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / acetonitrile / 20 - 45 °C 1.2: 0.5 h / 0 °C 2.1: toluene / 3 h / 100 °C 3.1: water; recombinant aminotransferase from Arthobacter sp.; pyridoxal 5'-phosphate; isopropylamine / dimethyl sulfoxide / 8 h / 45 °C / pH 8.5 / Enzymatic reaction View Scheme

: 209995-38-0
(2,4,5-trifluorophenyl)acetic acid

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: butyl (R)-3-amino-4-(2,4,5-trifluorophenyl)butanoate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / acetonitrile / 20 - 45 °C 1.2: 0.5 h / 0 °C 2.1: toluene / 3 h / 100 °C 3.1: water; recombinant aminotransferase from Arthobacter sp.; pyridoxal 5'-phosphate; isopropylamine / dimethyl sulfoxide / 8 h / 45 °C / pH 8.5 / Enzymatic reaction View Scheme

: 209995-38-0
(2,4,5-trifluorophenyl)acetic acid

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: isopropyl (R)-3-amino-4-(2,4,5-trifluorophenyl)butanoate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / acetonitrile / 20 - 45 °C 1.2: 0.5 h / 0 °C 2.1: toluene / 3 h / 100 °C 3.1: water; recombinant aminotransferase from Arthobacter sp.; pyridoxal 5'-phosphate; isopropylamine / dimethyl sulfoxide / 8 h / 45 °C / pH 8.5 / Enzymatic reaction View Scheme

: 209995-38-0
(2,4,5-trifluorophenyl)acetic acid

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: benzyl (R)-3-amino-4-(2,4,5-trifluorophenyl)butanoate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / acetonitrile / 20 - 45 °C 1.2: 0.5 h / 0 °C 2.1: toluene / 3 h / 100 °C 3.1: water; recombinant aminotransferase from Arthobacter sp.; pyridoxal 5'-phosphate; isopropylamine / dimethyl sulfoxide / 8 h / 45 °C / pH 8.5 / Enzymatic reaction View Scheme

: 209995-38-0
(2,4,5-trifluorophenyl)acetic acid

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: 2-hydroxyethyl (R)-3-amino-4-(2,4,5-trifluorophenyl)butanoate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / acetonitrile / 20 - 45 °C 1.2: 0.5 h / 0 °C 2.1: 3 h / 100 °C 3.1: water; recombinant aminotransferase from Arthobacter sp.; pyridoxal 5'-phosphate; isopropylamine / dimethyl sulfoxide / 8 h / 45 °C / pH 8.5 / Enzymatic reaction View Scheme

: 209995-38-0
(2,4,5-trifluorophenyl)acetic acid

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: 1151240-91-3
(3R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine; pivaloyl chloride / acetonitrile / 20 - 45 °C 1.2: 0.5 h / 0 °C 2.1: toluene / 3 h / 100 °C 3.1: water; recombinant aminotransferase from Arthobacter sp.; pyridoxal 5'-phosphate; isopropylamine / dimethyl sulfoxide / 8 h / 45 °C / pH 8.5 / Enzymatic reaction View Scheme

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

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: (R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid propyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 3 h / 100 °C 2: water; recombinant aminotransferase from Arthobacter sp.; pyridoxal 5'-phosphate; isopropylamine / dimethyl sulfoxide / 8 h / 45 °C / pH 8.5 / Enzymatic reaction View Scheme

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

A: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

B: butyl (R)-3-amino-4-(2,4,5-trifluorophenyl)butanoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 3 h / 100 °C 2: water; recombinant aminotransferase from Arthobacter sp.; pyridoxal 5'-phosphate; isopropylamine / dimethyl sulfoxide / 8 h / 45 °C / pH 8.5 / Enzymatic reaction View Scheme

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

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

Conditions

Conditions	Yield
With hydrogenchloride In ethanol optical yield given as %ee;	100%

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: C14H13F3N2O4

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 2h; Reflux;	95%

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: 24424-99-5
di-tert-butyl dicarbonate

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

Conditions

Conditions	Yield
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%

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: 486460-21-3
3-trifluoromethyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

: 486460-32-6
sitagliptin

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol In ethanol; dichloromethane at 10 - 25℃; for 3h;	86%

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

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

: C25H26F6N2O5

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20 - 30℃; Reagent/catalyst;	70%

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: 486460-32-6
sitagliptin

: C26H23F9N6O2

Conditions

Conditions	Yield
With dmap; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 80 - 90℃; for 24h;	65%

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: 24424-99-5
di-tert-butyl dicarbonate

: C20H26F3NO6

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 5h;	60%

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: C7H14N2O

A: C17H22F3O2N3

B: C17H22F3O2N3

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile

...Expand

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: C15H22N2O2

A: C25H30F3O3N3

B: C25H30F3O3N3

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile

...Expand

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: C8H13N2OF3

A: C18H21F6O2N3

B: C18H21F6O2N3

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile

...Expand

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: 1-tert-butyl-1,4-diazepan-2-one

A: C20H28F3O2N3

B: C20H28F3O2N3

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile

...Expand

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: 842104-09-0
C9H16N2O

A: C19H24N3O2F3

B: C19H24N3O2F3

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide

...Expand

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: 842103-96-2
C7H14N2O

: C17H22N3O2F3

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: 842103-82-6
C7H14N2O

: C17H22N3O2F3

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: C7H14N2O

: C17H22N3O2F3

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: C9H16N2O

A: C19H24F3O2N3

B: C19H24F3O2N3

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile

...Expand

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: ((R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)-butanoyl]-3-(t-butoxymethyl)piperazin-2-one)

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / methanol / 6 h / 0 - 20 °C 2.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 1.17 h / 0 °C 2.2: 1 h / 0 °C 3.1: hydrogenchloride; sodium hydrogencarbonate / dichloromethane; isopropyl alcohol View Scheme

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: (R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-(t-butoxymethyl)piperazin-2-one L-tartrate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate / methanol / 6 h / 0 - 20 °C 2.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 1.17 h / 0 °C 2.2: 1 h / 0 °C 3.1: hydrogenchloride; sodium hydrogencarbonate / dichloromethane; isopropyl alcohol 4.1: isopropyl alcohol; ethanol; water; acetone / 0.5 h View Scheme

: 936630-57-8
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

: t-butyl (R)-4-[(R)-2-(t-butoxymethyl)-3-oxopiperazin-1-yl]-4-oxo-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / methanol / 6 h / 0 - 20 °C 2.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 1.17 h / 0 °C 2.2: 1 h / 0 °C View Scheme

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

The cas register number of (R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid is 936630-57-8. It also can be called as benzenebutanoic acid, beta-amino-2,4,5-trifluoro-, (betaR)- and the Systematic name about this chemical is (3R)-3-ammonio-4-(2,4,5-trifluorophenyl)butanoate.

Physical properties about (R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid are: (1)ACD/LogP: 1.50 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -0.99 ; (4)ACD/LogD (pH 7.4): -1 ; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 37.3Å²; (13)Index of Refraction: 1.513; (14)Molar Refractivity: 50.1 cm³; (15)Molar Volume: 166.5 cm³; (16)Surface Tension: 45.6 dyne/cm; (17)Density: 1.399 g/cm³; (18)Flash Point: 151.3 °C; (19)Enthalpy of Vaporization: 60.05 kJ/mol; (20)Boiling Point: 326.6 °C at 760 mmHg; (21)Vapour Pressure: 8.67E-05 mmHg at 25°C.

People can use the following data to convert to the molecule structure.
1.SMILES: Fc1cc(c(F)cc1F)C[C@@H]([NH3+])CC([O-])=O
2.InChI: InChI=1/C10H10F3NO2/c11-7-4-9(13)8(12)2-5(7)1-6(14)3-10(15)16/h2,4,6H,1,3,14H2,(H,15,16)/t6-/m1/s1
3.InChIKey: KEFQQJVYCWLKPL-ZCFIWIBFBG
4.Std. InChI: InChI=1S/C10H10F3NO2/c11-7-4-9(13)8(12)2-5(7)1-6(14)3-10(15)16/h2,4,6H,1,3,14H2,(H,15,16)/t6-/m1/s1

Product Name

(R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid

Synthetic route

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

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