Benzyl 4-oxo-2-(s)-[[(phenylmethoxy)carbonyl]amino]butanoate

Base Information

• Chemical Name: Benzyl 4-oxo-2-(s)-[[(phenylmethoxy)carbonyl]amino]butanoate
• CAS No.: 58578-45-3
• Molecular Formula: C19H19 N O5
• Molecular Weight: 341.364
• European Community (EC) Number: 611-698-7
• DSSTox Substance ID: DTXSID70552480
• Nikkaji Number: J1.743.902B
• Wikidata: Q72441700
• Mol file: 58578-45-3.mol

Synonyms:58578-45-3;benzyl 4-oxo-2-(s)-[[(phenylmethoxy)carbonyl]amino]butanoate;4-Oxo-2S-[[(phenymethyoxy)carbonyl]amino]-butyric acid phenymethyl ester;benzyl (2S)-4-oxo-2-(phenylmethoxycarbonylamino)butanoate;(S)-Benzyl 2-(((benzyloxy)carbonyl)amino)-4-oxobutanoate;Benzyl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-oxobutanoate;(2S)-2-(benzyloxycarbonylamino)-4-oxobutyric acid benzyl ester;SCHEMBL16862505;DTXSID70552480;EX-A3774;MFCD11044892;(S)-4-Oxo-2-[[(phenylmethoxy)carbonyl]amino]butanoic acid phenylmethyl ester;s10946;BS-52214;(S)-Benzyl 2-(cbz-amino)-4-oxobutanoate;CS-0158786;EN300-640673;Benzyl (S)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoate;4-Oxo-2S-[[(phenylmethyloxy)carbonyl]amino]-butyric acid phenylmethyl ester (CbZ-L-Ala(For)-OBZl)

Chemical Property of Benzyl 4-oxo-2-(s)-[[(phenylmethoxy)carbonyl]amino]butanoate

Chemical Property:

• Vapor Pressure: 1.74E-11mmHg at 25°C
• Melting Point: 80.5-82 ºC
• Boiling Point: 534.1°C at 760 mmHg
• PKA: 10.47±0.46(Predicted)
• Flash Point: 276.8°C
• PSA: 81.70000
• Density: 1.223
• LogP: 3.00470
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 341.12632271
• Heavy Atom Count: 25
• Complexity: 428

Purity/Quality:

98%,99%, ^*data from raw suppliers

Benzyl 4-oxo-2-N-(S)-cbz butanoate ^*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)C(CC=O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@H](CC=O)NC(=O)OCC2=CC=CC=C2

Technology Process of Benzyl 4-oxo-2-(s)-[[(phenylmethoxy)carbonyl]amino]butanoate

There total 12 articles about Benzyl 4-oxo-2-(s)-[[(phenylmethoxy)carbonyl]amino]butanoate 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: 100.0%

benzyl L-2-<(carbobenzxyloxy)amino>-4-hydroxybutyrate (58578-44-2) → (2S)-2-(benzyloxycarbonylamino)-4-oxobutyric acid benzyl ester (58578-45-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

Reference yield: 65.0%

C31H43NO5S → (2S)-2-(benzyloxycarbonylamino)-4-oxobutyric acid benzyl ester (58578-45-3)

Guidance literature:

C₃₁H₄₃NO₅S; With 5% palladium on Al₂O₃; In acetonitrile; at 22 - 23 ℃; for 0.25h; Inert atmosphere;

With triethylsilane; In acetonitrile; Reagent/catalyst; Inert atmosphere;

Reference yield:

benzyl (3S)-2-oxotetrahydro-3-furanylcarbamate (35677-89-5) → (2S)-2-(benzyloxycarbonylamino)-4-oxobutyric acid benzyl ester (58578-45-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium hydroxide; water / 24 h / 60 °C

1.2: 20 °C / pH Ca_. 3

2.1: N,N-dimethyl-formamide / 21 h / 20 °C / Inert atmosphere

3.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

With water; sodium acetate; pyridinium chlorochromate; potassium hydroxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1071/CH13309

upstream raw materials:

benzyl L-2-<(carbobenzxyloxy)amino>-4-hydroxybutyrate

benzyl bromide

benzyl chloroformate

N-benzyloxycarbonyl-(L)-homoserine

Downstream raw materials:

(2S)-2-benzyloxycarbonylamino-4-oxo-hexanedioic acid 1-benzyl ester 6-ethyl ester

Refernces

• 1、 -. "MACROCYCLIC COMPOUNDS AS PROTEASOME INHIBITORS". Paragraph 0250. . Retrieved 2019/05/02.
• 2、 -. "CYCLOBUTANE- AND AZETIDINE-CONTAINING MONO AND SPIROCYCLIC COMPOUNDS AS ALPHA V INTEGRIN INHIBITORS". Page/Page column 108-110. . Retrieved 2018/05/27.