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

Base Information

• Chemical Name: (2S,4R)-4-(benzyl)di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate
• CAS No.: 127949-74-0
• Molecular Formula: C₂₁H₂₉NO₅
• Molecular Weight: 375.465
• Mol file: 127949-74-0.mol

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

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

There total 5 articles about (2S,4R)-4-(benzyl)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: 72.0%

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3) + benzyl bromide (100-39-0) → (2S,4R)-4-(benzyl)di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate (127949-74-0)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(98)00174-9

Reference yield:

(2S,4S)-4-(Hydroxy-phenyl-methyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester → (2S,4R)-4-(benzyl)di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate (127949-74-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 5h; under 2585.7 Torr;

DOI:10.1016/0040-4039(95)00450-Q

Reference yield:

L-t-butyl pyroglutamate (35418-16-7,85136-12-5) → (2S,4R)-4-(benzyl)di-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate (127949-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap / acetonitrile / 48.58 h / 0 - 20 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

With dmap; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm201533b

upstream raw materials:

di-tert-butyl dicarbonate

tert-butyl (2S)-4α-(phenylmethyl)pyroglutamate

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

benzyl bromide

Downstream raw materials:

menthol (2S)-4-benzylpyroglutamate

C₂₁H₃₁NO₄

γ-benzyl-L-proline

(2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid