(S)-2-tert-Butoxycarbonylamino-5-oxo-decanoic acid benzyl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-5-oxo-decanoic acid benzyl ester
• CAS No.: 131550-52-2
• Molecular Formula: C₂₂H₃₃NO₅
• Molecular Weight: 391.508
• Mol file: 131550-52-2.mol

Synonyms:(S)-2-tert-Butoxycarbonylamino-5-oxo-decanoic acid benzyl ester

Chemical Property of (S)-2-tert-Butoxycarbonylamino-5-oxo-decanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-5-oxo-decanoic acid benzyl ester

There total 6 articles about (S)-2-tert-Butoxycarbonylamino-5-oxo-decanoic 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: 92.0%

(S)-6-tert-Butoxycarbonylamino-2-butyl-3-oxo-heptanedioic acid 1-allyl ester 7-benzyl ester (131550-45-3) → (S)-2-tert-Butoxycarbonylamino-5-oxo-decanoic acid benzyl ester (131550-52-2)

Guidance literature:

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 25 ℃; for 18h;

DOI:10.1016/S0040-4039(00)97050-3

Reference yield:

Boc-Glu-OBn (30924-93-7) → (S)-2-tert-Butoxycarbonylamino-5-oxo-decanoic acid benzyl ester (131550-52-2)

Guidance literature:

Multi-step reaction with 4 steps

1: N-methylmorpholine / tetrahydrofuran / 0.5 h / -15 °C

2: Et₃N / tetrahydrofuran / 1 h / -15 °C

3: iodoform / CCl₄ / 3 h / Irradiation

4: 1.) CuCN, LiCl, lithium naphthalenide / 1.) THF, -78 deg C, 30 min, 2.) THF, -30 deg C, 3 h

With 4-methyl-morpholine; iodoform; triethylamine; naphthalen-1-yl-lithium; lithium chloride; In tetrahydrofuran; tetrachloromethane;

DOI:10.1039/a802142b

Reference yield:

(S)-2-tert-Butoxycarbonylamino-5-oxo-heptanedioic acid 7-allyl ester 1-benzyl ester (131550-31-7) → (S)-2-tert-Butoxycarbonylamino-5-oxo-decanoic acid benzyl ester (131550-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / Na₂CO₃ / dimethylformamide / 18 h / 60 °C

2: 92 percent / pyrrolidine / Pd(PPh₃)4 / acetonitrile / 18 h / 25 °C

With pyrrolidine; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(00)97050-3

upstream raw materials:

(S)-6-tert-Butoxycarbonylamino-2-butyl-3-oxo-heptanedioic acid 1-allyl ester 7-benzyl ester

Hexanoyl chloride

(S)-2-((tert-butoxycarbonyl)amino)-4-iodobutyric acid benzyl ester

Boc-Glu-OBn