(2S)-5-Oxo-2-pyrrolidinecarbothioic Acid S-Ethyl Ester

Base Information

• Chemical Name: (2S)-5-Oxo-2-pyrrolidinecarbothioic Acid S-Ethyl Ester
• CAS No.: 1298024-11-9
• Molecular Formula: C₇H₁₁NO₂S
• Molecular Weight: 173.236
• Mol file: 1298024-11-9.mol

Synonyms:

Chemical Property of (2S)-5-Oxo-2-pyrrolidinecarbothioic Acid S-Ethyl Ester

Chemical Property:

• Boiling Point: 365.9±31.0 °C(Predicted)
• PKA: 14.41±0.40(Predicted)
• Density: 1.211±0.06 g/cm3(Predicted)

Purity/Quality:

(2S)-5-Oxo-2-pyrrolidinecarbothioicAcidS-EthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-5-Oxo-2-pyrrolidinecarbothioic Acid S-Ethyl Ester

There total 1 articles about (2S)-5-Oxo-2-pyrrolidinecarbothioic Acid S-Ethyl 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: 71.0%

ethanethiol (75-08-1) + L-Pyroglutamic acid (98-79-3) → (5S)-pyrrolidin-2-one-5-carbothioic acid ethyl ester (1298024-11-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;

DOI:10.1021/ol200743u

Reference yield: 83.0%

di-tert-butyl dicarbonate (24424-99-5) + (5S)-pyrrolidin-2-one-5-carbothioic acid ethyl ester (1298024-11-9) → (5S)-N-(tert-butyloxycarbonyl)pyrrolidin-2-one-5-carbothioic acid ethyl ester (1298023-90-1)

Guidance literature:

With dmap; In acetonitrile; at 0 - 20 ℃;

DOI:10.1021/ol200743u

Reference yield:

(5S)-pyrrolidin-2-one-5-carbothioic acid ethyl ester (1298024-11-9) → (S)-5-oxopyrrolidine-2-carbaldehyde (96914-00-0)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap / acetonitrile / 2 h / 20 °C / Cooling with ice

2: palladium on activated charcoal / acetone / 1 h / 20 °C / Cooling with ice

3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C / Cooling with ice

With dmap; palladium on activated charcoal; trifluoroacetic acid; In dichloromethane; acetone; acetonitrile;

upstream raw materials:

ethanethiol

L-Pyroglutamic acid

Downstream raw materials:

(5S)-N-(tert-butyloxycarbonyl)pyrrolidin-2-one-5-carbothioic acid ethyl ester

(S)-5-oxopyrrolidine-2-carbaldehyde

Refernces

• 1、 Hoye, Adam T.,Wipf, Peter. "Total synthesis of (-)-sessilifoliamide C and (-)-8-epi-stemoamide". supporting information; experimental part. p. 2634 - 2637. Retrieved 2011/07/09.