Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate

Base Information

• Chemical Name: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate
• CAS No.: 154456-97-0
• Molecular Formula: C17H21NO5
• Molecular Weight: 319.357
• Mol file: 154456-97-0.mol

Synonyms:2-benzyl 1-tert-butyl (2S)-4-oxo-1,2-pyrrolidinecarboxylate;(S)-2-benzyl 1-tert-butyl 4-oxopyrrolidine-1,2-dicarboxylate;benzyl (2S,4R)-N-tert-butoxycarbonyl-4-oxoprolinate;benzyl Nα-Boc-4-keto-L-prolinate;benzyl (2S)-N-tert-butoxycarbonyl-4-oxoprolinate;benzyl (S)-1-tert-butoxycarbonyl-4-oxopyrrolidine-2-carboxylate;

Chemical Property of Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate

Chemical Property:

• Boiling Point: 439.9±45.0 °C(Predicted)
• PKA: -3.90±0.40(Predicted)
• PSA: 72.91000
• Density: 1.219±0.06 g/cm3(Predicted)
• LogP: 2.24620

Purity/Quality:

98%,99%, ^*data from raw suppliers

BOC-L-PRO(4-OXO)-O-BN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate

There total 11 articles about Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate 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: 94.0%

N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester (89813-47-8) → 2-benzyl 1-(tert-butyl) (S)-4-oxopyrrolidine-1,2-dicarboxylate (154456-97-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.75h;

DOI:10.1021/acs.joc.8b02920

Reference yield: 77.0%

C19H27NO6S → dimethyl sulfoxide (67-68-5,8070-53-9) + 2-benzyl 1-(tert-butyl) (S)-4-oxopyrrolidine-1,2-dicarboxylate (154456-97-0)

Guidance literature:

tetrakis(trifluoroacetato)rhodium(II); In 1,2-dichloro-ethane; for 6h; Heating;

DOI:10.1039/c39930001434

Reference yield:

(2R,2R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl-ester 1-tert-butyl ester + sodium hydrogencarbonate (144-55-8) → 2-benzyl 1-(tert-butyl) (S)-4-oxopyrrolidine-1,2-dicarboxylate (154456-97-0)

Guidance literature:

With triethylamine; In dichloromethane; dimethyl sulfoxide;

upstream raw materials:

benzyl bromide

N-tert-butoxycarbonyl-4-oxo-L-proline

N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

(2S,4S)-1-[(tert-butoxy)carbonyl]-4-(trifluoromethyl)pyrrolidine-2-carboxylic acid

(2S,4S)-N-tert-butoxycarbonyl-4-difluoromethylproline

2-benzyl 1-(tert-butyl) (S)-4-(trifluoromethyl)-2.5-dihydro-1H-pyrrole-1.2-dicarboxylate

benzyl (2S,4S)-N-tert-butoxycarbonyl-4-hydroxy-4-trifluoromethylprolinate

Refernces

• 1、 -. "Tetrahydropyridopyrimidine compound with anti-tumor activity". Paragraph 0604-0608. . Retrieved 2020/12/30.
• 2、 -. "FLUOROHYDROXYPROLINE DERIVATIVES USEFUL IN THE PREPARATION OF PROTEOLYSIS TARGETED CHIMERAS". Page/Page column 46; 72. . Retrieved 2018/04/14.