(2S,4S)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

Base Information

• Chemical Name: (2S,4S)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester
• CAS No.: 148587-50-2
• Molecular Formula: C₂₀H₂₅NO₇
• Molecular Weight: 391.421

Synonyms:(2S,4S)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

Chemical Property of (2S,4S)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

Chemical Property:

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Technology Process of (2S,4S)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

There total 1 articles about (2S,4S)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl 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:

bromoacetic acid tert-butyl ester (5292-43-3) + N-methoxycarbonyl (S)-pyroglutamic acid benzylester (146356-00-5) → (2S,4S)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester (148587-50-2) + (2S,4R)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester (148587-49-9)

Guidance literature:

With lithium hexamethyldisilazane; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, -78 deg C, 2) -78 deg C, 1 h;

DOI:10.1016/S0040-4039(00)60445-8

Reference yield: 86.0%

(2S,4S)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester (148587-50-2) → (2S,4S)-4-tert-Butoxycarbonylmethyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

Guidance literature:

With diisobutylaluminium hydride; In hexane;

DOI:10.1016/S0040-4039(00)60445-8

Reference yield: 40.0%

(2S,4S)-4-tert-Butoxycarbonylmethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester (148587-50-2) → (2S,4S)-4-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester (148587-44-4)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)60445-8

upstream raw materials:

bromoacetic acid tert-butyl ester

N-methoxycarbonyl (S)-pyroglutamic acid benzylester

Downstream raw materials:

(2S,4S)-4-tert-Butoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

(2S,4S)-4-(carboxymethyl)pyrrolidine-2-carboxylic acid

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