(S)-Benzyl (1-cyano-2-phenylethyl)carbamate

Base Information

• Chemical Name: (S)-Benzyl (1-cyano-2-phenylethyl)carbamate
• CAS No.: 21947-21-7
• Molecular Formula: C17H16N2O2
• Molecular Weight: 280.326
• ChEMBL ID: CHEMBL4587430
• DSSTox Substance ID: DTXSID30555199
• Nikkaji Number: J859.536D
• Wikidata: Q72516354
• Mol file: 21947-21-7.mol

Synonyms:21947-21-7;(S)-Benzyl (1-cyano-2-phenylethyl)carbamate;BENZYL N-[(1S)-1-CYANO-2-PHENYLETHYL]CARBAMATE;(S)-benzyl 1-cyano-2-phenylethylcarbamate;(S)-Benzyl(1-cyano-2-phenylethyl)carbamate;SCHEMBL392814;CHEMBL4587430;DTXSID30555199;Carbamic acid, N-[(1S)-1-cyano-2-phenylethyl]-, phenylmethyl ester;AKOS005146167;AKOS015840715;Benzyl [(1S)-1-cyano-2-phenylethyl]carbamate

Chemical Property of (S)-Benzyl (1-cyano-2-phenylethyl)carbamate

Chemical Property:

• Melting Point: 135-136 °C
• Refractive Index: 1.58
• Boiling Point: 494.929 °C at 760 mmHg
• Flash Point: 253.124 °C
• PSA: 62.12000
• Density: 1.175 g/cm³
• LogP: 3.43858
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 280.121177757
• Heavy Atom Count: 21
• Complexity: 362

Purity/Quality:

98%min ^*data from raw suppliers

(S)-Benzyl(1-cyano-2-phenylethyl)carbamate 95+% ^*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#N)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C#N)NC(=O)OCC2=CC=CC=C2

Technology Process of (S)-Benzyl (1-cyano-2-phenylethyl)carbamate

There total 8 articles about (S)-Benzyl (1-cyano-2-phenylethyl)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%

benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate (5241-56-5,17324-88-8,53562-23-5,4801-80-3) → (S)-N-benzyloxycarbonyl-2-amino-3-phenyl-propionitrile (21947-21-7)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield: 95.0%

benzyl (1S)-(1-formyl-2-phenylethyl)carbamate (59830-60-3) → (S)-N-benzyloxycarbonyl-2-amino-3-phenyl-propionitrile (21947-21-7)

Guidance literature:

With ammonium hydroxide; iodine; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/jo0625352

Reference yield:

N-Cbz-L-Phe (1161-13-3) → (S)-N-benzyloxycarbonyl-2-amino-3-phenyl-propionitrile (21947-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: ethyl chloroformate; aq. ammonia; triethylamine / tetrahydrofuran / 0.5 h / 0 °C

2: 7.7 g / phosphorus oxychloride; pyridine / 0 - 20 °C

With pyridine; ammonium hydroxide; chloroformic acid ethyl ester; triethylamine; trichlorophosphate; In tetrahydrofuran;

DOI:10.1021/ol0708020

upstream raw materials:

benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate

benzyl (1S)-(1-formyl-2-phenylethyl)carbamate

L-phenylalanine

N-Cbz-L-Phe

Downstream raw materials:

(S)-5-[1-(benzyloxycarbonylamino)-2-phenyl-ethyl]-2H-tetrazole

(S)-2-phenyl-1-(1H-tetrazol-5-yl)ethan-1-amine

C₉H₁₁N₅*C₂HF₆NO₄S₂

L-Phenylalanine amide

Refernces

• 1、 Cappiello, John R.,Chen, Emily,Dillon, Nicholas,Hull, Mitchell V.,Kitamura, Seiya,Kitamura, Shinichi,Kotaniguchi, Miyako,Nizet, Victor,Sharpless, K. Barry,Solania, Angelo,Woehl, Jordan L.,Wolan, Dennis W.,Zheng, Qinheng. "Sulfur(VI) Fluoride Exchange (SuFEx)-Enabled High-Throughput Medicinal Chemistry". supporting information. p. 10899 - 10904. Retrieved 2020/07/13.
• 2、 Chitale, Sampada,Derasp, Joshua S.,Hussain, Bashir,Tanveer, Kashif,Beauchemin, André M.. "Carbohydrates as efficient catalysts for the hydration of α-amino nitriles". supporting information. p. 13147 - 13150. Retrieved 2016/11/09.