N-carbobenzoxypyroglutamyl diazomethyl ketone

Base Information

• Chemical Name: N-carbobenzoxypyroglutamyl diazomethyl ketone
• CAS No.: 81910-23-8
• Molecular Formula: C₁₄H₁₃N₃O₄
• Molecular Weight: 287.275
• Mol file: 81910-23-8.mol

Synonyms:1-Pyrrolidinecarboxylicacid, 2-(diazoacetyl)-5-oxo-, phenylmethyl ester, (S)-

Chemical Property of N-carbobenzoxypyroglutamyl diazomethyl ketone

Chemical Property:

• PSA: 97.82000
• LogP: 2.37708

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-carbobenzoxypyroglutamyl diazomethyl ketone

There total 2 articles about N-carbobenzoxypyroglutamyl diazomethyl ketone 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:

Cbz-L-pGlu-OH (32159-21-0) → (S)-N-Benzyloxycarbonyl-5-diazoacetylpyrrolidin-2-one (81910-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / tetrahydrofuran / 3 h / 20 °C

2: 8.68 g / KOH / tetrahydrofuran; diethyl ether

With potassium hydroxide; oxalyl dichloride; In tetrahydrofuran; diethyl ether;

DOI:10.1039/b005516f

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (S)-N-Benzyloxycarbonylpyroglutamic acid chloride (61177-53-5) → (S)-N-Benzyloxycarbonyl-5-diazoacetylpyrrolidin-2-one (81910-23-8)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; diethyl ether;

DOI:10.1039/b005516f

Reference yield: 78.0%

acetic acid (64-19-7,77671-22-8) + (S)-N-Benzyloxycarbonyl-5-diazoacetylpyrrolidin-2-one (81910-23-8) → (S)-5-Acetoxyacetyl-N-benzoyloxycarbonylpyrrolidin-2-one (319915-99-6)

Guidance literature:

for 1h; Heating;

DOI:10.1039/b005516f

upstream raw materials:

diazomethane

(S)-N-Benzyloxycarbonylpyroglutamic acid chloride

Cbz-L-pGlu-OH

Downstream raw materials:

(S)-5-Acetoxyacetyl-N-benzoyloxycarbonylpyrrolidin-2-one

Refernces