benzyl chloroformate
3-amino propanoic acid
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0 - 20℃; | 99% |
With sodium carbonate In 1,4-dioxane; water at 20℃; | 96% |
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; | 92% |
3-[(N-benzyloxycarbonyl)amino]propanol
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With NADH oxidase; horse liver alcohol dehydrogenase Enzymatic reaction; | 10% |
Conditions | Yield |
---|---|
With L-Phenylalanine amide; sodium chloride; calcium chloride In N,N-dimethyl-formamide at 25℃; for 3h; pH=8; aq. buffer; | A 7.4% B n/a |
3-(benzyloxycarbonylamino)-propionic acid methyl ester
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
succinic acid anhydride
benzyl alcohol
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
(i) tBu3SnN3, dioxane, (ii) /BRN= 878307/, (iii) aq. NaOH; Multistep reaction; | |
(i) nBu3SnN3, THF, (ii) /BRN= 878307/; Multistep reaction; |
N-carbobenzoxy-β-alanine-p-nitrophenyl ester
A
4-nitro-phenol
B
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With 1H-imidazole; water In ethanol at 25℃; Mechanism; Kinetics; phosphate buffer (pH=8.05); |
N-benzyloxycarbonyl-L-aspartic acid anhydride
A
3-(benzyloxycarbonylamino)propanoic acid
B
N-Cbz-Ala
Conditions | Yield |
---|---|
With hydrogenchloride; bis(1,5-cyclooctadiene)nickel (0); N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran for 8h; Product distribution; Heating; Further complex ligands.; | |
With hydrogenchloride; [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) 1.) THF, reflux, 8h.; Yield given. Multistep reaction. Yields of byproduct given; | |
With hydrogenchloride; bis(1,5-cyclooctadiene)nickel (0); N,N,N,N,-tetramethylethylenediamine 1.) THF, reflux, 8h.; Yield given. Multistep reaction. Yields of byproduct given; |
3-(((benzyloxy)carbonyl)amino)propionic tert-butyl ester
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With trifluoroacetic acid for 0.5h; |
1-diazo-3-(N-benzyloxycarbonyl)amino-2-propanone
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
silver trifluoroacetate In 1,4-dioxane; water for 0.5h; Wolff rearrangement; sonication; | |
With silver benzoate In 1,4-dioxane; water at 110℃; under 3102.97 Torr; for 0.0166667h; Wolff rearrangement; Microwave irradiation; Closed vessel; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: ClCOOEt; N-methylmorpholine / tetrahydrofuran / 0.25 h / -15 °C 1.2: tetrahydrofuran; CH2Cl2 / -15 - 20 °C 2.1: CF3COOAg / dioxane; H2O / 0.5 h / sonication View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N / 0.17 h / 20 °C 2: CF3CO2H / 0.5 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine 2: aq.-ethanolic NaOH View Scheme |
benzyl chloroformate
3-amino propanoic acid
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In sodium hydroxide; toluene |
N-(benzyloxycarbonyl)-β-alanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl)methyl ester
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
In methanol for 8.55h; Kinetics; Wavelength; Time; UV-irradiation; aq. HEPES buffer; |
N-(benzyloxycarbonyl)-L-β-alanine (6-methoxy-2-oxo-2H-benzo[h]benzopyran-4-yl)methyl ester
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
In methanol for 7.3h; Kinetics; Wavelength; Time; UV-irradiation; aq. HEPES buffer; |
C19H18N2O5
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With methanol for 0.0566667h; pH=7.2; Kinetics; Wavelength; Time; UV-irradiation; aq. HEPES buffer; |
C23H20N2O5
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With methanol for 0.08h; pH=7.2; Kinetics; Wavelength; Time; UV-irradiation; aq. HEPES buffer; |
C23H20N2O7
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With methanol for 0.463333h; pH=7.2; Kinetics; Wavelength; Time; UV-irradiation; aq. HEPES buffer; |
C23H20N2O7
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With methanol for 0.46h; pH=7.2; Kinetics; Wavelength; Time; UV-irradiation; aq. HEPES buffer; |
3-benzyloxycarbonylaminopropionic acid benzyl ester
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 1h; |
A
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
In methanol for 0.0666667h; pH=7.2; Quantum yield; Kinetics; Solvent; Time; Wavelength; Irradiation; |
3-[(N-benzyloxycarbonyl)amino]propanol
A
3-(benzyloxycarbonylamino)propanoic acid
B
3-[(benzyloxycarbonyl)amino]propanal
Conditions | Yield |
---|---|
With chloroperoxidase from C. fumago; dihydrogen peroxide In aq. acetate buffer for 24h; pH=5.0; Kinetics; Time; Enzymatic reaction; | A 1.5 μmol B 11.5 μmol C n/a D 4.0 mg |
3-[(N-benzyloxycarbonyl)amino]propanol
A
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dihydrogen peroxide; chloroperoxidase from C. fumago / aq. acetate buffer / 24 h / pH 5.0 / Enzymatic reaction 2: dihydrogen peroxide; chloroperoxidase from C. fumago / aq. acetate buffer / 19 h / pH 5.0 / Enzymatic reaction View Scheme |
tert.-butylhydroperoxide
3-[(N-benzyloxycarbonyl)amino]propanol
A
3-(benzyloxycarbonylamino)propanoic acid
B
3-[(benzyloxycarbonyl)amino]propanal
Conditions | Yield |
---|---|
With chloroperoxidase from C. fumago In aq. acetate buffer for 7h; pH=5.0; Kinetics; Time; Enzymatic reaction; | A 2.6 μmol B 16.1 μmol C n/a |
3-[(benzyloxycarbonyl)amino]propanal
A
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With chloroperoxidase from C. fumago; dihydrogen peroxide In aq. acetate buffer for 19h; pH=5.0; Kinetics; Enzymatic reaction; |
tert.-butylhydroperoxide
3-[(benzyloxycarbonyl)amino]propanal
A
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With chloroperoxidase from C. fumago In aq. acetate buffer for 19h; pH=5.0; Kinetics; Enzymatic reaction; |
2-(Trimethylsilyl)ethanol
3-(benzyloxycarbonylamino)propanoic acid
3-Benzyloxycarbonylamino-propionic acid 2-trimethylsilanyl-ethyl ester
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere; | 100% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane |
cycl-isopropylidene malonate
3-(benzyloxycarbonylamino)propanoic acid
[3-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-3-oxo-propyl]-carbamic acid benzyl ester
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere; | 100% |
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 4.08333h; Inert atmosphere; |
3-(benzyloxycarbonylamino)propanoic acid
N-[(phenylmethoxy)carbonyl]-β-alanine chloride
Conditions | Yield |
---|---|
With oxalyl dichloride In dichloromethane at 25℃; for 4h; | 99% |
With oxalyl dichloride In dichloromethane at 20 - 25℃; for 4h; | 99% |
With oxalyl dichloride In dichloromethane at 20℃; for 6h; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 16h; Product distribution / selectivity; | 99% |
With potassium carbonate In acetone at 60℃; for 16h; Product distribution / selectivity; | 99% |
With potassium carbonate In [(2)H6]acetone at 20 - 60℃; for 16h; Reflux; | 99% |
With potassium carbonate In acetone Reflux; | 99% |
With potassium carbonate In acetone for 18h; Heating; |
3-(benzyloxycarbonylamino)propanoic acid
benzyl (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 16h; | 99% |
Conditions | Yield |
---|---|
With potassium fluoride In N,N-dimethyl-formamide at 20℃; | 99% |
Conditions | Yield |
---|---|
Stage #1: 3-(benzyloxycarbonylamino)propanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h; Stage #2: C34H47N5O5 In dichloromethane at 20℃; | 99% |
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 99% |
1-hydroxy-pyrrolidine-2,5-dione
3-(benzyloxycarbonylamino)propanoic acid
N-benzyloxycarbonyl-3-aminopropionic acid succinimide ester
Conditions | Yield |
---|---|
With polymer supported ethyl dimethylaminopropylcarbodiimide In chloroform; N,N-dimethyl-formamide for 14h; | 98% |
With dicyclohexyl-carbodiimide In 1,4-dioxane stirred overnight; | |
With dicyclohexyl-carbodiimide In acetonitrile for 2h; Ambient temperature; | |
With diisopropyl-carbodiimide In 1,4-dioxane for 2h; |
3-(benzyloxycarbonylamino)propanoic acid
8-(chloromethyl)-2-methyl-6-oxo-6H-benzopyrano[6,7-d]oxazole
C23H20N2O7
Conditions | Yield |
---|---|
With potassium fluoride In N,N-dimethyl-formamide at 20℃; for 24h; | 98% |
3-(benzyloxycarbonylamino)propanoic acid
4-amino-4-(2-tert-butoxycarbonylethyl)heptanedioic acid di-tertbutyl ester
Conditions | Yield |
---|---|
With HATU In N,N-dimethyl-formamide at 20℃; for 16h; | 98% |
With 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 16h; | 98% |
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
With copper diacetate; sodium carbonate; (3aR,3a'R,8aS,8a'S)-2,2'-(propane-2,2-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole) In dichloromethane; water at 30℃; for 12h; enantioselective reaction; | 97% |
3-(benzyloxycarbonylamino)propanoic acid
2’-carboxybenzoylpaclitaxel
2’-carboxybenzoyl-7-(N-carboxybenzoyl-β-alanyl)paclitaxel
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 20h; | 96% |
With dmap; dicyclohexyl-carbodiimide at 23℃; for 18h; Inert atmosphere; | 95% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 90.5% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride |
3-(benzyloxycarbonylamino)propanoic acid
dimethyl amine
N',N'-dimethyl-N-carbobenzoxy-β-alaninamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 24h; | 95% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 72h; | 90% |
(i) ClCO2Et, Et3N, CHCl3, (ii) /BRN= 605257/; Multistep reaction; | |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In 1,4-dioxane at 0℃; for 1.5h; |
3-(benzyloxycarbonylamino)propanoic acid
2,3,4,5,6-pentafluorophenol
Z-β-alanine pentafluorophenyl ester
Conditions | Yield |
---|---|
With polymer supported ethyl dimethylaminopropylcarbodiimide In chloroform; N,N-dimethyl-formamide for 14h; | 95% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ethyl acetate | 87% |
With dicyclohexyl-carbodiimide In ethyl acetate; N,N-dimethyl-formamide at 0 - 5℃; |
Conditions | Yield |
---|---|
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform for 16h; | 95% |
methanol
3-(benzyloxycarbonylamino)propanoic acid
3-(benzyloxycarbonylamino)-propionic acid methyl ester
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 20℃; for 12h; | 95% |
With hydrogenchloride for 0.333333h; Heating; | 22.7 g |
3-(benzyloxycarbonylamino)propanoic acid
allyl bromide
2-propen-1-yl 3-(phenylmethoxycarbonylamino)propanoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; | 95% |
With potassium carbonate In acetone Reflux; | 95% |
3-(benzyloxycarbonylamino)propanoic acid
2-(bromomethyl)-8-methyl-6-oxo-6H-benzopyrano[6,7-d]oxazole
C23H20N2O7
Conditions | Yield |
---|---|
With potassium fluoride In N,N-dimethyl-formamide at 20℃; for 5h; | 95% |
mono-tert-butyl malonate
3-(benzyloxycarbonylamino)propanoic acid
Conditions | Yield |
---|---|
Stage #1: 3-(benzyloxycarbonylamino)propanoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 25℃; for 18h; Stage #2: mono-tert-butyl malonate With isopropylmagnesium chloride In tetrahydrofuran at 0 - 40℃; for 5.5h; | 95% |
3-(benzyloxycarbonylamino)propanoic acid
[2-(2-carbamoyl-1-methyl-vinylamino)-ethyl]-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: 3-(benzyloxycarbonylamino)propanoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In dichloromethane at 0℃; for 0.0833333h; Stage #2: [2-(2-carbamoyl-1-methyl-vinylamino)-ethyl]-carbamic acid tert-butyl ester With dmap In dichloromethane at 0 - 20℃; for 1h; | 95% |
3-amino-propionic acid ethyl ester
3-(benzyloxycarbonylamino)propanoic acid
N-(N-benzyloxycarbonyl-β-alanyl)-β-alanine ethyl ester
Conditions | Yield |
---|---|
With 1-ethyl-piperidine; dicyclohexyl-carbodiimide In dichloromethane 1) -5 deg C; 2) 0 deg C, 2 h; 3) 12h, room temp.; | 93% |
3-(benzyloxycarbonylamino)propanoic acid
1-O-allyl-2,3-di-O-benzyl-6-O-tosyl-β-D-glucose
1-O-allyl-2,3-di-O-benzyl-4-O-(carbobenzoxy-β-alanyl)-6-O-tosyl-β-D-glucopyranoside
Conditions | Yield |
---|---|
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h; | 93% |
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 89% |
3-(benzyloxycarbonylamino)propanoic acid
(S)-2-amino-N1,N5-didodecylpentanediamide
N',N"-didodecyl-Nα-[(3-(N'''-benzyloxycarbonyl)amino)propanoyl]-L-glutamide
Conditions | Yield |
---|---|
With diethyl cyanophosphonate; triethylamine In tetrahydrofuran at 20℃; for 24h; | 93% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; | 93% |
3-(benzyloxycarbonylamino)propanoic acid
N-Cbz-3-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl olean-12-en-28-oate-3-yl)oxy-3-oxopropylamine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 12h; | 93% |
1-aza-18-crown-6
3-(benzyloxycarbonylamino)propanoic acid
N-<3-propanoyl>-1-aza-18-crown-6
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; | 92% |
3-(benzyloxycarbonylamino)propanoic acid
NG-2,2,5,7,8-pentamethylchroman-6-sulfonyl-L-arginine
N-α-[N-(benzyloxycarbonyl)-β-alanyl]-N-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)arginine
Conditions | Yield |
---|---|
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 12h; Condensation; | 92% |
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide 1.) DMF, room temperature, overnight, 2.) room temperature, overnight; Yield given; Multistep reaction; |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; | 92% |
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