(S)-2-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester
• CAS No.: 208519-99-7
• Molecular Formula: C₁₈H₂₃N₃O₅
• Molecular Weight: 361.398
• Mol file: 208519-99-7.mol

Synonyms:(S)-2-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester

Chemical Property of (S)-2-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester

There total 3 articles about (S)-2-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester 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: 71.0%

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate (113400-36-5,400626-71-3) + diazomethyl-trimethyl-silane (18107-18-1) → (S)-2-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester (208519-99-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -105 - -100 ℃; for 0.166667h;

Reference yield:

Boc-Glu-OBn (30924-93-7) → (S)-2-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester (208519-99-7)

Guidance literature:

Multi-step reaction with 2 steps

1: N-methylmorpholine / ethyl acetate / 3 h / -20 °C

2: diethyl ether / 16 h / Ambient temperature

With 4-methyl-morpholine; In diethyl ether; ethyl acetate;

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (S)-2-tert-Butoxycarbonylamino-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester → (S)-2-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester (208519-99-7)

Guidance literature:

In diethyl ether; for 16h; Ambient temperature;

upstream raw materials:

diazomethane

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

diazomethyl-trimethyl-silane

Boc-Glu-OBn

Downstream raw materials:

(S)-4-(2-Amino-thiazol-4-yl)-2-tert-butoxycarbonylamino-butyric acid benzyl ester

Refernces

• 1、 Patt, William C.,Skeean, Richard W.,Steinbaugh, Bruce A.. "Synthesis of Enantiomerically Pure Amino Acids Containing a 2-Amino-4-thiazolyl Side Chain". . p. 3097 - 3102. Retrieved 2007/10/02.