Boc-D-Phenylglycine supplier | CasNO.33125-05-2

Name
Boc-D-Phenylglycine
EINECS 1533716-785-6
CAS No. 33125-05-2
Article Data77
CAS DataBase
Density 1.182 g/cm³
Solubility Insoluble in water. Slightly soluble in DMSO and methanol.
Melting Point 88-91 °C
Formula C₁₃H₁₇NO₄
Boiling Point 407.2 °C at 760 mmHg
Molecular Weight 251.282
Flash Point 200.1 °C
Transport Information
Appearance
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Benzeneaceticacid, a-[[(1,1-dimethylethoxy)carbonyl]amino]-,(R)-;(R)-N-Boc-2-amino-2-phenylaceticacid;(R)-[(tert-Butoxycarbonyl)amino]phenylethanoicacid;BOC-D-Phg-OH;D-2-tert-Butoxycarboxamido-2-phenylacetic acid;N-(tert-Butoxycarbonyl)-D-2-phenylglycine;N-tert-Butyloxycarbonyl-D-phenylglycine;
PSA 66.84000
LogP 2.51270

Synthetic route

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

: 875-74-1
(R)-phenylglycine

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With sodium hydroxide In tert-butyl alcohol at 20℃; for 1h; Inert atmosphere;	100%
With potassium hydrogencarbonate In tetrahydrofuran; water for 18h;	99%
With sodium hydroxide	96%

: 875-74-1
(R)-phenylglycine

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; water for 18h;	94%

: 875-74-1
(R)-phenylglycine

: tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 25℃; for 12h;	89%

: 956101-46-5
tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile	85%

: 875-74-1
(R)-phenylglycine

: 50739-44-1
1-(t-butoxycarbonyl)-1,2,4-triazolo<4,3-a>pyridinium-3-olate

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With sodium hydroxide In acetone for 2h; Ambient temperature;	84%

: 2900-27-8, 3601-66-9, 14675-97-9, 33125-05-2
2-(tert-butoxycarbonylamino)-2-phenylacetic acid

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
	82%

: 125414-45-1
(2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With ruthenium trichloride; sodium periodate; sodium carbonate In tetrachloromethane; water; acetonitrile for 2h; Ambient temperature;	79%

: 67341-01-9, 117049-14-6, 138457-46-2, 102089-74-7
(R)-N-(tert-butoxycarbonyl)phenylglycinol

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile at 0 - 20℃; for 1h;	77%
With dipyridinium dichromate In N,N-dimethyl-formamide Ambient temperature;
With dipyridinium dichromate In N,N-dimethyl-formamide for 6h; Ambient temperature;

: C16H17F6NO4

A: 33125-05-2
Boc-D-Phg-OH

B: 2900-27-8
(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid

Conditions

Conditions	Yield
With C28H30N3O2(1+)*Br(1-); sodium hydroxide In chloroform at 0℃; for 24h;	A n/a B 35%

: 124-38-9
carbon dioxide

: 186375-61-1
N-(triisopropylsilyl)-N-(tert-butyloxycarbonyl)benzylamine

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Stage #1: N-(triisopropylsilyl)-N-(tert-butyloxycarbonyl)benzylamine With sec.-butyllithium; (-)-sparteine In diethyl ether; cyclohexane at -78℃; for 3h; Stage #2: carbon dioxide In diethyl ether; cyclohexane for 0.333333h;	7%

: 875-74-1
(R)-phenylglycine

: 59577-27-4
diethyl 2-tert-butoxycarbonyloxyiminomalonate

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With triethylamine In methanol; water Ambient temperature;

: 188200-11-5
(2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile for 2h;

: 124-38-9
carbon dioxide

: 186375-60-0
N-(trimethylsilyl)-N-(tert-butyloxycarbonyl)benzylamine

A: 33125-05-2
Boc-D-Phg-OH

B: 2900-27-8
(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid

Conditions

Conditions	Yield
With sec.-butyllithium; (-)-sparteine In hexane at -78℃; for 0.333333h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Stage #1: N-(trimethylsilyl)-N-(tert-butyloxycarbonyl)benzylamine With sec.-butyllithium; (-)-sparteine In cyclohexane; toluene at -78℃; for 3h; Stage #2: carbon dioxide In cyclohexane; toluene for 0.333333h; Title compound not separated from byproducts;

...Expand

: Boc-D-PhGly-ONp

A: 100-02-7
4-nitro-phenol

B: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With phosphate buffer; apomyoglobin In 1,4-dioxane at 4℃; pH=7.0; Enzyme kinetics; Further Variations:; Reagents;

: 137284-11-8, 138811-46-8, 140196-38-9
(2R)-2-N-(tert-butoxycarbonyl)amino-2-phenylethanal

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 20℃; for 2h;

: 685132-79-0
tert-butyl [(1R)-2-nitro-1-phenylethyl]carbamate

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
With acetic acid; sodium nitrite In dimethyl sulfoxide at 40℃; for 24h;
With acetic acid; sodium nitrite In dimethyl sulfoxide at 40℃; for 24h; Inert atmosphere;

: 4248-19-5
tert-butyl carbamate

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: formic acid / methanol; H2O / 72 h / 20 °C 2: anhydrous potassium carbonate / tetrahydrofuran / 17 h / Heating 3: 81 percent / ethyldiisopropylamine; anhydrous zinc triflate; (-)-(1R,2S)-N-methylephedrine / molecular sieves 4 Angstroem / -20 °C 4: sodium nitrite; acetic acid / dimethylsulfoxide / 24 h / 40 °C View Scheme

: 100-52-7
benzaldehyde

(E)-n-C6H13CH=CHZrCp2Cl: (E)-n-C6H13CH=CHZrCp2Cl

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: formic acid / methanol; H2O / 72 h / 20 °C 2: anhydrous potassium carbonate / tetrahydrofuran / 17 h / Heating 3: 81 percent / ethyldiisopropylamine; anhydrous zinc triflate; (-)-(1R,2S)-N-methylephedrine / molecular sieves 4 Angstroem / -20 °C 4: sodium nitrite; acetic acid / dimethylsulfoxide / 24 h / 40 °C View Scheme

: 150884-50-7
benzaldehyde N-boc imine

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / ethyldiisopropylamine; anhydrous zinc triflate; (-)-(1R,2S)-N-methylephedrine / molecular sieves 4 Angstroem / -20 °C 2: sodium nitrite; acetic acid / dimethylsulfoxide / 24 h / 40 °C View Scheme

: 155396-71-7
tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: anhydrous potassium carbonate / tetrahydrofuran / 17 h / Heating 2: 81 percent / ethyldiisopropylamine; anhydrous zinc triflate; (-)-(1R,2S)-N-methylephedrine / molecular sieves 4 Angstroem / -20 °C 3: sodium nitrite; acetic acid / dimethylsulfoxide / 24 h / 40 °C View Scheme

: 14371-10-9
(E)-3-phenylpropenal

(R)-p-mentha-1,5-diene: (R)-p-mentha-1,5-diene

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: diethyl ether; pentane / 4 h / -100 - -78 °C 1.2: aq. NaOH; aq. H2O2 / diethyl ether; pentane / 14 h / -78 - 20 °C 1.3: pyridine / CH2Cl2 / 1 h / 0 °C 2.1: 2.0 g / K2CO3 / methanol / 3 h / 20 °C 3.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -42 °C 3.2: tetrahydrofuran / 1 h / -42 - 20 °C 3.3: 89 percent / K2CO3 / xylene / 14 h / 150 °C 4.1: KOH / ethanol; H2O / 24 h / 20 °C 5.1: 1.1 g / diethyl ether / 3 h / 20 °C 6.1: O3 / CH2Cl2 / 3 h / -78 °C 6.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C 7.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: diethyl ether; pentane / 4 h / -100 - -78 °C
1.2: aq. NaOH; aq. H2O2 / diethyl ether; pentane / 14 h / -78 - 20 °C
1.3: pyridine / CH2Cl2 / 1 h / 0 °C
2.1: 2.0 g / K2CO3 / methanol / 3 h / 20 °C
3.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -42 °C
3.2: tetrahydrofuran / 1 h / -42 - 20 °C
3.3: 89 percent / K2CO3 / xylene / 14 h / 150 °C
4.1: KOH / ethanol; H2O / 24 h / 20 °C
5.1: 1.1 g / diethyl ether / 3 h / 20 °C
6.1: O3 / CH2Cl2 / 3 h / -78 °C
6.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C
7.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C
View Scheme

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

1.) NaH; 2.) SOCl2: 1.) NaH; 2.) SOCl2

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1.1 g / diethyl ether / 3 h / 20 °C 2.1: O3 / CH2Cl2 / 3 h / -78 °C 2.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C 3.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C View Scheme

: 172925-28-9
trans-(S)-1-phenyl-1,5-hexadien-3-ol

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -42 °C 1.2: tetrahydrofuran / 1 h / -42 - 20 °C 1.3: 89 percent / K2CO3 / xylene / 14 h / 150 °C 2.1: KOH / ethanol; H2O / 24 h / 20 °C 3.1: 1.1 g / diethyl ether / 3 h / 20 °C 4.1: O3 / CH2Cl2 / 3 h / -78 °C 4.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C 5.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -42 °C
1.2: tetrahydrofuran / 1 h / -42 - 20 °C
1.3: 89 percent / K2CO3 / xylene / 14 h / 150 °C
2.1: KOH / ethanol; H2O / 24 h / 20 °C
3.1: 1.1 g / diethyl ether / 3 h / 20 °C
4.1: O3 / CH2Cl2 / 3 h / -78 °C
4.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C
5.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C
View Scheme

: (E)-(S)-1-Phenyl-hexa-2,5-dienylamine

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1.1 g / diethyl ether / 3 h / 20 °C 2.1: O3 / CH2Cl2 / 3 h / -78 °C 2.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C 3.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C View Scheme

: (1S)-1-[(E)-2-phenylvinyl]but-3-enyl acetate

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 2.0 g / K2CO3 / methanol / 3 h / 20 °C 2.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -42 °C 2.2: tetrahydrofuran / 1 h / -42 - 20 °C 2.3: 89 percent / K2CO3 / xylene / 14 h / 150 °C 3.1: KOH / ethanol; H2O / 24 h / 20 °C 4.1: 1.1 g / diethyl ether / 3 h / 20 °C 5.1: O3 / CH2Cl2 / 3 h / -78 °C 5.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: 2.0 g / K2CO3 / methanol / 3 h / 20 °C
2.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -42 °C
2.2: tetrahydrofuran / 1 h / -42 - 20 °C
2.3: 89 percent / K2CO3 / xylene / 14 h / 150 °C
3.1: KOH / ethanol; H2O / 24 h / 20 °C
4.1: 1.1 g / diethyl ether / 3 h / 20 °C
5.1: O3 / CH2Cl2 / 3 h / -78 °C
5.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C
6.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C
View Scheme

: 849796-38-9
tert-butyl (1S,2E)-1-phenylhexa-2,5-dienylcarbamate

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: O3 / CH2Cl2 / 3 h / -78 °C 1.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C 2.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C View Scheme

: 849796-21-0
2,2,2-trichloro-N-[(1S,2E)-1-phenylhexa-1,5-dienyl]acetamide

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: KOH / ethanol; H2O / 24 h / 20 °C 2.1: 1.1 g / diethyl ether / 3 h / 20 °C 3.1: O3 / CH2Cl2 / 3 h / -78 °C 3.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C 4.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C View Scheme

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

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / acetonitrile; H2O / 1 h / 0 °C 2: 96 percent / H2 / Pd(OH)2/C / methanol / 1 h / 20 °C 3: 77 percent / NaIO4; RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: 82 percent / diisopropylethylamine / dioxane / 20 h / 50 °C 2: 94 percent / H2 / Pd(OH)2 / methanol / 72 h / 760 Torr / Ambient temperature 3: NaIO4, RuCl3*H2O / acetonitrile; CCl4; H2O / 2 h View Scheme
Multi-step reaction with 2 steps 1: 90 percent / H2 / Pd(OH)2/C / ethyl acetate 2: 79 percent / RuCl3, NaIO4, Na2CO3, / H2O; acetonitrile; CCl4 / 2 h / Ambient temperature View Scheme

: 162237-91-4
(R)-1-phenyl-2-(phenylmethoxy)ethylamine

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / acetonitrile; H2O / 1 h / 0 °C 2: 96 percent / H2 / Pd(OH)2/C / methanol / 1 h / 20 °C 3: 77 percent / NaIO4; RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / 0 - 20 °C View Scheme

: 510730-65-1
(2-benzyloxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester

: 33125-05-2
Boc-D-Phg-OH

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / H2 / Pd(OH)2/C / methanol / 1 h / 20 °C 2: 77 percent / NaIO4; RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / 0 - 20 °C View Scheme

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

: 33125-05-2
Boc-D-Phg-OH

: 39249-27-9
N-(tert-butoxycarbonyl)-D-phenylglycine N-succinimido ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In 1,4-dioxane	100%
With dicyclohexyl-carbodiimide In tetrahydrofuran for 43h;	98%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide for 18h;

: 33125-05-2
Boc-D-Phg-OH

: 94838-59-2
tert-butyl 4-aminophenethylcarbamate

: 849540-68-7
(R)-[4-(2-tert-butoxycarbonylaminoethyl)phenylcarbamoyl]phenyl-methylcarbamic acid tert-butyl ester

Conditions

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0℃; for 1.58333h; Product distribution / selectivity;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 21.1667h; Product distribution / selectivity;

: (R)-tert-butyl 2-(((2-(2-(methylthio)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzo[d]oxazol-4-yl)oxy)methyl)pyrrolidine-1-carboxylate

: 33125-05-2
Boc-D-Phg-OH

: tert-butyl ((R)-2-((R)-2-(((2-(2-(methylthio)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzo[d]oxazol-4-yl)oxy)methyl)pyrrolidin-1-yl)-2-oxo-1-phenylethyl)carbamate

Conditions

Conditions	Yield
Stage #1: (R)-tert-butyl 2-(((2-(2-(methylthio)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzo[d]oxazol-4-yl)oxy)methyl)pyrrolidine-1-carboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: Boc-D-Phg-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;	100%

Yield

Stage #1: (R)-tert-butyl 2-(((2-(2-(methylthio)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzo[d]oxazol-4-yl)oxy)methyl)pyrrolidine-1-carboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
Stage #2: Boc-D-Phg-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;

100%

: 33125-05-2
Boc-D-Phg-OH

: 4-(4-(trans-4-benzyloxycarbonylaminocyclohexyl)phenyl)-2-((S)-1-t-butoxylcarbonylpyrrolidin-2-yl)imidazole

: (2S)-2-(4-(trans-4-benzyloxycarbonylaminocyclohexyl)phenylimidazol-2-yl)-1-((R)-2-t-butoxycarbonylamino-2-phenylacetyl)pyrrolidine

Conditions

Conditions	Yield
Stage #1: 4-(4-(trans-4-benzyloxycarbonylaminocyclohexyl)phenyl)-2-((S)-1-t-butoxylcarbonylpyrrolidin-2-yl)imidazole With hydrogenchloride In ethanol; chloroform; ethyl acetate at 20 - 60℃; for 2.5h; Stage #2: Boc-D-Phg-OH With N-ethyl-N,N-diisopropylamine; HATU In ethyl acetate; N,N-dimethyl-formamide at 0℃; for 1h;	100%

: 110-91-8
morpholine

: 33125-05-2
Boc-D-Phg-OH

: tert-butyl (R)-2-morpholino-2-oxo-1-phenylethylcarbamate

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide	99%
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Inert atmosphere; Stage #2: morpholine In dichloromethane for 12h; Inert atmosphere;

: 33125-05-2
Boc-D-Phg-OH

: 74-89-5
methylamine

: tert-butyl (R)-(methylcarbamoyl)(phenyl)methylcarbamate

Conditions

Conditions	Yield
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran; water at -20℃; for 1h;	99%
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h; Stage #2: methylamine In tetrahydrofuran at -20℃; for 2h;	96%
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h; Stage #2: methylamine In tetrahydrofuran; water at -20℃; for 2h;	96%

: N-((2Z)-3-methyl-4-(-1-piperazinylmethyl)-1,3-thiazol-2(3H)-ylidene)methanamine trihydrochloride

: 33125-05-2
Boc-D-Phg-OH

: tert-butyl (1R)-2-(4-(((2Z)-3-methyl-2-(methylimino)-2,3-dihydro-1,3-thiazol-4-yl)methyl)-1-piperazinyl)-2-oxo-1-phenylethylcarbamate

Conditions

Conditions	Yield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.25h; Stage #2: N-((2Z)-3-methyl-4-(-1-piperazinylmethyl)-1,3-thiazol-2(3H)-ylidene)methanamine trihydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine at 20℃; for 15h;	99%

: 33125-05-2
Boc-D-Phg-OH

: 75460-19-4
benzyl 7β-amino-3-methyl-1,2-dehydro-1-carba-1-dethia-3-cephem-4-carboxylate

: (6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methyl-8-oxo-1-aza-bicyclo[4.2.0]octa-2,4-diene-2-carboxylic acid

Conditions

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran for 1h; Ambient temperature;	98%

: 33125-05-2
Boc-D-Phg-OH

: 67347-43-7
(1R,2R)-(-)-trans-2-pyrrolidinyl-N-methylcyclohexylamine

: 125073-01-0
{(R)-[Methyl-((1R,2R)-2-pyrrolidin-1-yl-cyclohexyl)-carbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With pyridine; dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Ambient temperature;	97%

: 33125-05-2
Boc-D-Phg-OH

: 67198-53-2
trans-N-methyl-2-(1-pyrrolidinyl)-cyclohexanamine

: 125072-99-3
{(R)-[Methyl-((1S,2S)-2-pyrrolidin-1-yl-cyclohexyl)-carbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With pyridine; dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Ambient temperature;	97%

: 33125-05-2
Boc-D-Phg-OH

: 70491-05-3
(2R)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid

Conditions

Conditions	Yield
With hydrogen In ethyl acetate at 80℃; under 7600.51 Torr; for 48h; Autoclave;	97%

: 33125-05-2
Boc-D-Phg-OH

: 29833-32-7
11-aminoundecanoic acid methyl ester hydrochloride

: 805230-91-5
methyl 11-({(2R)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoyl}amino)undecanoate

Conditions

Conditions	Yield
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	96%

: 33125-05-2
Boc-D-Phg-OH

: 124780-55-8
methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside

: 131751-03-6
methyl 6,7-anhydro-2,3-di-O-benzyl-4-O-(2-t-butoxycarbonylamino-2-phenylacetyl)-8-deoxy-α-D-threo-D-galacto-octoside

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrachloromethane for 3h;	95%

: 33125-05-2
Boc-D-Phg-OH

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 819796-91-3
2(R)-N-(tert-butoxycarbonyl)-N'-methoxy-N'-methylphenylglycinamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	94%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	52%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	52%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃;
Stage #1: Boc-D-Phg-OH With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 2h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 18.5h; Cooling;

: 5813-64-9
2,2-dimethylpropylamine

: 33125-05-2
Boc-D-Phg-OH

: (R)-2-N-Boc-N-neopentyl-2-phenylacetamide

Conditions

Conditions	Yield
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h; Stage #2: 2.2-dimethylpropylamine In tetrahydrofuran at -20℃; for 2h;	94%
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h; Stage #2: 2.2-dimethylpropylamine In tetrahydrofuran; water at -20℃; for 2h;	94%

: 33125-05-2
Boc-D-Phg-OH

: C14H21N3OS

: tert-butyl (R)-2-((S)-2-(4-cyclohexylthiazol-2-ylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate

Conditions

Conditions	Yield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol In dichloromethane at 20℃; for 0.166667h; Stage #2: C14H21N3OS With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	93.1%

: 33125-05-2
Boc-D-Phg-OH

: 62284-41-7, 73951-73-2
(6R,7S)-7-Amino-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

: 76284-31-6
(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Conditions

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran	93%

: 856417-67-9
5-methyl-2-(piperazin-1-yl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one

: 33125-05-2
Boc-D-Phg-OH

: 856417-24-8
tert-butyl 2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethylcarbamate

Conditions

Conditions	Yield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.25h; Stage #2: 5-methyl-2-(piperazin-1-yl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one With triethylamine In acetonitrile at 20℃; for 15h; Product distribution / selectivity;	93%

: 33125-05-2
Boc-D-Phg-OH

: 109-73-9
N-butylamine

: (R)-2-N-Boc-N-(n-butyl)-2-phenylacetamide

Conditions

Conditions	Yield
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h; Stage #2: N-butylamine In tetrahydrofuran at -20℃; for 2h;	93%
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h; Stage #2: N-butylamine In tetrahydrofuran; water at -20℃; for 2h;	93%

: 33125-05-2
Boc-D-Phg-OH

: 75-64-9
tert-butylamine

: 926293-43-8
(R)-t-butyl (2-(t-butylamino)-2-oxo-1-phenylethyl)carbamate

Conditions

Conditions	Yield
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere;	93%
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h; Stage #2: tert-butylamine In tetrahydrofuran at -20℃; for 2h;	74%

: C12H19N3OS

: 33125-05-2
Boc-D-Phg-OH

: tert-butyl (R)-2-((S)-2-(4-tert-butylthiazol-2-ylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate

Conditions

Conditions	Yield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol In dichloromethane at 20℃; for 0.166667h; Stage #2: C12H19N3OS With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	92.9%

: 33125-05-2
Boc-D-Phg-OH

: (2R,4S,5R)-1-benzyl-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide

: O(9)-Boc-D-phenylglycineyl-N-benzylcinchoninium bromide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	92.7%

: 33125-05-2
Boc-D-Phg-OH

: (6R,7S)-7-Amino-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

: 76284-38-3
(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Conditions

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran	92%

: 33125-05-2
Boc-D-Phg-OH

: C30H36N4O7

: Boc-D-Phg-D-Asp(OBn)-D-Pro-Acpc-Phe-OMe, Phg - 2-amino-2-phenylacetic acid, Acpc - 1-aminocyclopropane carboxylic acid

Conditions

Conditions	Yield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 23℃; for 12h;	92%

: 33125-05-2
Boc-D-Phg-OH

: C9H13N3OS

: tert-butyl (R)-2-((S)-2-(4-methylthiazol-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate

Conditions

Conditions	Yield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol In dichloromethane at 20℃; for 0.166667h; Stage #2: C9H13N3OS With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	91.2%

: 67-56-1
methanol

: 33125-05-2
Boc-D-Phg-OH

: 19883-41-1
D-phenylglycine methyl ester hydrochloride

Conditions

Conditions	Yield
With chloro-trimethyl-silane at 20℃; for 45h; Esterification; de-tert-butoxycarbonylation;	91%

: 33125-05-2
Boc-D-Phg-OH

: 768370-32-7
(5R,6R,1'S)-6-amino-1-[1-(naphthalen-1-yl)ethyl]-1-azaspiro[4.4]nonan-2-one

: (1R,6'R,1''R)-{[1-(1-naphthalen-2-ylethyl)-2-oxo-1-azaspiro[4.4]non-6-ylcarbamoyl]phenylmethyl}carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1.5h;	91%

: 2-methyl-5-(1-piperazinyl)imidazo[1,2-a]pyridine dihydrochloride

: 33125-05-2
Boc-D-Phg-OH

: 856418-67-2
tert-butyl (1R)-2-(4-(2-methylimidazo[1,2-a]pyridin-5-yl)-1-piperazinyl)-2-oxo-1-phenylethylcarbamate

Conditions

Conditions	Yield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.25h; Stage #2: 2-methyl-5-(1-piperazinyl)imidazo[1,2-a]pyridine dihydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In acetonitrile at 20℃; for 15h;	91%

Boc-D-Phenylglycine Chemical Properties

The Molecular formula of Boc-D-Phg-OH(33125-05-2): C₁₃H₁₇NO₄
The Molecular Weight of Boc-D-Phg-OH(33125-05-2): 251.2784
The Molecular Structure of Boc-D-Phg-OH(2900-27-8):

Index of Refraction: 1.532
Molar Refractivity: 65.86 cm³
Molar Volume: 212.5 cm³
Polarizability: 26.11 10 ^-24 cm³
Surface Tension: 45.2 dyne/cm
Boiling Point: 407.2 °C at 760 mmHg
Density: 1.182 g/cm³
Flash Point: 200.1 °C
Enthalpy of Vaporization: 69.49 kJ/mol
Vapour Pressure: 2.32E-07 mmHg at 25°C

Boc-D-Phenylglycine Safety Profile

The Safety Statements information of Boc-D-Phg-OH(33125-05-2):
24/25: Avoid contact with skin and eyes
WGK Germany: 3

Product Name

Boc-D-Phenylglycine

Synthetic route

Boc-D-Phenylglycine Chemical Properties

Boc-D-Phenylglycine Safety Profile

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