Benzyl N-(2-amino-1-phenylethyl)carbamate

Base Information

• Chemical Name: Benzyl N-(2-amino-1-phenylethyl)carbamate
• CAS No.: 142854-51-1
• Molecular Formula: C₁₆H₁₈N₂O₂
• Molecular Weight: 270.331
• DSSTox Substance ID: DTXSID90453147
• Mol file: 142854-51-1.mol

Synonyms:142854-51-1;Benzyl N-(2-amino-1-phenylethyl)carbamate;benzyl (2-amino-1-phenylethyl)carbamate;Carbamic acid, (2-amino-1-phenylethyl)-, phenylmethyl ester;[1-(AMINOMETHYL)-2-PHENYLETHYL]-CARBAMIC ACID PHENYLMETHYL ESTER;Benzyl (2-amino-1-phenylethyl)carbamate oxalate;(R)-N-Cbz-2-amino-1-phenylethylamine;SCHEMBL10979333;DTXSID90453147;MFCD21091398;AKOS015955229;AB88724;AB89386;benzyl(2-amino-1-phenylethyl)carbamate;FT-0769842

Chemical Property of Benzyl N-(2-amino-1-phenylethyl)carbamate

Chemical Property:

• PSA: 67.84000
• LogP: 3.51750
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 270.136827821
• Heavy Atom Count: 20
• Complexity: 284

Purity/Quality:

99.90% ^*data from raw suppliers

Benzyl(2-amino-1-phenylethyl)carbamate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CN)C2=CC=CC=C2

Technology Process of Benzyl N-(2-amino-1-phenylethyl)carbamate

There total 16 articles about Benzyl N-(2-amino-1-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: 87.0%

(S)-2-<(benzyloxycarbonyl)amino>-2-phenyl ethyl azide (190393-65-8) → ((S)-2-Amino-1-phenyl-ethyl)-carbamic acid benzyl ester (130406-36-9,142854-51-1)

Guidance literature:

(S)-2-<(benzyloxycarbonyl)amino>-2-phenyl ethyl azide; With triphenylphosphine; In tetrahydrofuran; for 8h; Reflux;

With water; In tetrahydrofuran; for 16h; Reflux;

DOI:10.1039/c2ob25693b

Reference yield:

(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid (2900-27-8) → ((S)-2-Amino-1-phenyl-ethyl)-carbamic acid benzyl ester (130406-36-9,142854-51-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / tetrahydrofuran

2.1: triethylamine / dichloromethane

3.1: sodium azide / N,N-dimethyl-formamide / 60 °C

4.1: hydrogenchloride; methanol

5.1: triethylamine / dichloromethane

6.1: triphenylphosphine / tetrahydrofuran / 8 h / Reflux

6.2: 16 h / Reflux

With hydrogenchloride; methanol; sodium azide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c2ob25693b

Reference yield:

N-[(benzyloxy)carbonyl]-(R)-β-amino-1-azido-2-phenylethane (130406-38-1) → Nβ-<(benzyloxy)carbonyl>-(R)-β-amino-2-phenylethanamine (130406-35-8,142854-51-1)

Guidance literature:

With Lindlar's catalyst; hydrogen; In ethyl acetate; at 30 ℃; for 6h; under 2327.2 Torr;

DOI:10.1021/jm00105a062

upstream raw materials:

N-[(benzyloxy)carbonyl]-(R)-β-amino-1-azido-2-phenylethane

D-2-phenylglycinol

(R)-benzyl [2-hydroxy-1-phenylethyl]carbamate

toluene-4-sulfonic acid (R)-2-benzyloxycarbonylamino-2-phenyl-ethyl ester

Downstream raw materials:

9H-fluoren-9-ylmethyl -3-(1H-indol-3-ylmethyl)-4,9-dioxo-7,11-diphenyl-10-oxa-2,5,8-triazaundecanoate

9H-fluoren-9-ylmethyl -3-(1H-indol-3-ylmethyl)-3-methyl-4,9-dioxo-7,11-diphenyl-10-oxa-2,5,8-triazaundecanoate

Refernces

• 1、 Sureshbabu, Vommina V.,Naik, Shankar A.,Hemantha,Narendra,Das, Ushati,Guru Row, Tayur N.. "N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides". supporting information; experimental part. p. 5260 - 5266. Retrieved 2009/12/06.