Z-PHE-ALA-DIAZOMETHYLKETONE

Base Information

• Chemical Name: Z-PHE-ALA-DIAZOMETHYLKETONE
• CAS No.: 71732-53-1
• Molecular Formula: C21H22 N4 O4
• Molecular Weight: 394.43
• Mol file: 71732-53-1.mol

Synonyms:Carbamicacid, [(1S)-2-[[(1S)-3-diazo-1-methyl-2-oxopropyl]amino]-2-oxo-1-(phenylmethyl)ethyl]-,phenylmethyl ester (9CI); Carbamic acid,[2-[(3-diazo-1-methyl-2-oxopropyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-,phenylmethyl ester, [S-(R*,R*)]-

Chemical Property of Z-PHE-ALA-DIAZOMETHYLKETONE

Chemical Property:

• PSA: 125.62000
• LogP: 4.19848
• Storage Temp.: -15°C

Purity/Quality:

99%+, ^*data from raw suppliers

Z-Phe-Ala-diazomethylketone,99% 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-PHE-ALA-DIAZOMETHYLKETONE

There total 2 articles about Z-PHE-ALA-DIAZOMETHYLKETONE 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + N-benzyloxycarbonyl-L-phenylalanyl-L-alanine (3338-39-4,16088-00-9,16088-38-3,17563-25-6,55387-02-5,80996-16-3,21881-18-5) → (Z,3S)-1-diazonio-3-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]but-1-en-2-olate carbamic acid (71732-53-1)

Guidance literature:

N-benzyloxycarbonyl-L-phenylalanyl-L-alanine; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -25 - -15 ℃; for 1h; Inert atmosphere;

diazomethane; With sodium hydroxide; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 4h; Inert atmosphere;

DOI:10.1002/chem.201103322

Reference yield:

N-benzyloxycarbonyl-L-phenylalanyl-L-alanine (3338-39-4,16088-00-9,16088-38-3,17563-25-6,55387-02-5,80996-16-3,21881-18-5) → (Z,3S)-1-diazonio-3-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]but-1-en-2-olate carbamic acid (71732-53-1)

Guidance literature:

Multi-step reaction with 2 steps

2: diethyl ether

In diethyl ether; 1: Condensation / 2: Diazotization;

DOI:10.1039/a907948c

Reference yield:

(Z,3S)-1-diazonio-3-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]but-1-en-2-olate carbamic acid (71732-53-1) → [(S)-1-((S)-1-Methyl-2,3-dioxo-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (150074-36-5)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at 20 ℃;

DOI:10.1016/S0040-4039(99)02267-4

upstream raw materials:

N-benzyloxycarbonyl-L-phenylalanyl-L-alanine

diazomethane

Downstream raw materials:

[(S)-1-((S)-1-Methyl-2,3-dioxo-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester

Z-L-phenylalanyl-L-alanyl bromomethyl ketone

Refernces

• 1、 Darkins, Paul,Groarke, Michelle,McKervey, M. Anthony,Moncrieff, Hazel M.,McCarthy, Noreen,Nieuwenhuyzen, Mark. "Enantiopure N-protected α-amino glyoxals 1. Synthesis from α-amino acids and some condensation reactions with amines". . p. 381 - 389. Retrieved 2007/10/03.