(2S,4R)-4-(4-tert-butylbenzyl)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S,4R)-4-(4-tert-butylbenzyl)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate
• CAS No.: 1609006-17-8
• Molecular Formula: C₂₅H₃₇NO₅
• Molecular Weight: 431.572
• Mol file: 1609006-17-8.mol

Synonyms:(2S,4R)-4-(4-tert-butylbenzyl)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate

Chemical Property of (2S,4R)-4-(4-tert-butylbenzyl)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-(4-tert-butylbenzyl)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate

There total 1 articles about (2S,4R)-4-(4-tert-butylbenzyl)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate 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: 44.0%

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3) + 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene (18880-00-7) → (2S,4R)-4-(4-tert-butylbenzyl)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate (1609006-17-8)

Guidance literature:

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.75h; Inert atmosphere;

1-(bromomethyl)-4-(1,1-dimethylethyl)benzene; In tetrahydrofuran; at -78 ℃; for 1h; diastereospecific reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.03.016

Reference yield: 94.0%

(2S,4R)-4-(4-tert-butylbenzyl)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate (1609006-17-8) → (2R,4S)-2-(4-tert-butylbenzyl)-5-tert-butoxy-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid (1609006-19-0)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at -10 - -5 ℃; for 1h;

DOI:10.1016/j.tetasy.2014.03.016

Reference yield:

(2S,4R)-4-(4-tert-butylbenzyl)-di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate (1609006-17-8) → (2S,4R)-tert-butyl 4-(4-tert-butylbenzyl)-2-((tert-butoxycarbonyl)amino)-5-(ethylamino)-5-oxopentanoate (1609006-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium hydroxide; water / tetrahydrofuran / 1 h / -10 - -5 °C

2: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With water; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; lithium hydroxide; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2014.03.016

upstream raw materials:

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

1-(bromomethyl)-4-(1,1-dimethylethyl)benzene

Downstream raw materials:

(2R,4S)-2-(4-tert-butylbenzyl)-5-tert-butoxy-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid

(2S,4R)-tert-butyl 4-(4-tert-butylbenzyl)-2-((tert-butoxycarbonyl)amino)-5-(ethylamino)-5-oxopentanoate

(2S,4R)-4-(4-tert-butylbenzyl)-2-amino-5-(ethylamino)-5-oxopentanoic acid