(S)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate

Base Information

• Chemical Name: (S)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate
• CAS No.: 4801-80-3
• Molecular Formula: C₁₇H₁₈N₂O₃
• Molecular Weight: 298.342
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID301164989
• Nikkaji Number: J80.905E
• Pharos Ligand ID: QHMR375TM8VH
• ChEMBL ID: CHEMBL2042018
• Mol file: 4801-80-3.mol

Synonyms:4801-80-3;Z-PHE-NH2;(S)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate;CHEMBL2042018;benzyl N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate;N-Alpha-Carbobenzoxy-L-phenylalanine amide;Z-Phe-NH;Z-L-Phenylalanine amide;Cbz-Phe-NH2;Z--Phe--NH2;SCHEMBL764062;HHBOFAIEPRHUSR-HNNXBMFYSA-N;DTXSID301164989;BDBM50041558;MFCD00077028;AKOS004910430;AM82178;AS-46913;CS-0213361;F10897;N-alpha-Benzyloxycarbonyl-L-phenylalanine amide;A871994;Nalpha -[(Phenylmethoxy)carbonyl]-L-phenylalaninamide;(S)-benzyl 1-amino-1-oxo-3-phenylpropan-2-ylcarbamate;(S)-Benzyl(1-amino-1-oxo-3-phenylpropan-2-yl)carbamate;Benzyl (S)-(1-amino-1-oxo-3-phenylpropan-2-yl)carbamate;Phenylmethyl N-[(1S)-2-amino-2-oxo-1-(phenylmethyl)ethyl]carbamate;Phenylmethyl?N-[(1S)-2-amino-2-oxo-1-(phenylmethyl)ethyl]carbamate

Chemical Property of (S)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate

Chemical Property:

• Melting Point: 165-166 °C(Solv: chloroform (67-66-3); heptane (142-82-5))
• Boiling Point: 356.9oC at 760 mmHg
• PKA: 11.13±0.46(Predicted)
• Flash Point: 169.7oC
• PSA: 81.42000
• Density: 1.143 g/cm3
• LogP: 3.10060
• Storage Temp.: Store at RT.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 298.13174244
• Heavy Atom Count: 22
• Complexity: 361

Purity/Quality:

99% ^*data from raw suppliers

Z-L-phenylalanine amide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)N)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)N)NC(=O)OCC2=CC=CC=C2

Technology Process of (S)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate

There total 39 articles about (S)-Benzyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

N-Cbz-L-Phe (1161-13-3) → benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate (5241-56-5,17324-88-8,53562-23-5,4801-80-3)

Guidance literature:

N-Cbz-L-Phe; With N-hydroxy-5-norbornene-2,3-dicarboxylic acid imide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 0 - 35 ℃; for 4h;

With ammonia; In N,N-dimethyl-formamide; acetonitrile; at 0 ℃; for 4h;

Reference yield: 82.0%

methyl 2-(((benzyloxy)carbonyl)amino)-3-phenylpropanoate (32563-40-9) → benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate (5241-56-5,17324-88-8,53562-23-5,4801-80-3) + methyl (R)-2-(benzyloxycarbonylamino)-3-phenylpropanoate (37440-07-6)

Guidance literature:

With ammonium chloride; triethylamine; In tert-butyl alcohol; at 35 ℃; for 10h; Alcalase alkaline protease was used;

DOI:10.1055/s-1993-25955

Reference yield: 80.0%

{(S)-1-[(R)-1-Amino-3-(tert-butyl-diphenyl-silanyloxy)-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester (928406-71-7) → [(S)-1-((R)-1-Amino-3-hydroxy-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (928406-72-8) + benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate (5241-56-5,17324-88-8,53562-23-5,4801-80-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmcl.2006.10.017

upstream raw materials:

H-Phe-OEt

benzyl chloroformate

N-Benzyloxycarbonyl-L-phenylalanin-

N-Cbz-L-Phe

Downstream raw materials:

(S)-benzyl (1-(tert-butylamino)-1-oxo-3-phenylpropan-2-yl)carbamate

Z-Phe-ΔAla

2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-oxo-butyric acid methyl ester

2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-malonic acid dimethyl ester

Refernces

• 1、 Moreno-Cinos, Carlos,Sassetti, Elisa,Salado, Irene G.,Witt, Gesa,Benramdane, Siham,Reinhardt, Laura,Cruz, Cristina D.,Joossens, Jurgen,Van Der Veken, Pieter,Br?tz-Oesterhelt, Heike,Tammela, P?ivi,Winterhalter, Mathias,Gribbon, Philip,Windshügel, Bj?rn,Augustyns, Koen. "α-Amino Diphenyl Phosphonates as Novel Inhibitors of Escherichia coli ClpP Protease". . p. 774 - 797. Retrieved 2019/01/30.
• 2、 Ezawa, Tetsuya,Kawashima, Yuya,Noguchi, Takuya,Jung, Seunghee,Imai, Nobuyuki. "Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1S,2R)-tranylcypromine". . p. 1690 - 1699. Retrieved 2017/11/14.