(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester
• CAS No.: 401564-36-1
• Molecular Formula: C13H20N2O4S
• Molecular Weight: 300.379
• Mol file: 401564-36-1.mol

Synonyms:1-Pyrrolidinecarboxylic acid, 4-oxo-2-(3-thiazolidinylcarbonyl)-,1,1-dimethylethyl ester, (2S)-;(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester;(S)-tert-Butyl 4-oxo-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate;(S)-tert-butyl 3-oxo-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate;

Chemical Property of (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester

Chemical Property:

• Boiling Point: 492℃
• PKA: -1.22±0.20(Predicted)
• Flash Point: 251℃
• PSA: 92.22000
• Density: 1.305
• LogP: 0.97360
• Storage Temp.: 2-8°C

Purity/Quality:

99.0%, High purity. ^*data from raw suppliers

(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic Acid 1,1-Dimethylethyl Ester is an intermediate used to prepare dipeptidyl peptidase IV (DPP-IV) inhibitors.

Technology Process of (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester

There total 13 articles about (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl 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: 90.0%

1,3-thiazolidine (504-78-9) + (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (102195-80-2) → (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester (401564-36-1)

Guidance literature:

With acetic acid; In methanol; at 0 - 30 ℃; for 2.5h; Large scale;

Reference yield: 89.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-mercaptoethylamine hydrochloride (156-57-0) + N-tert-butoxycarbonyl-4-oxo-L-proline (84348-37-8) → (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester (401564-36-1)

Guidance literature:

2-mercaptoethylamine hydrochloride; N-tert-butoxycarbonyl-4-oxo-L-proline; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

formaldehyd; In dichloromethane; water; at 10 - 20 ℃; for 10h; Temperature;

Reference yield: 86.0%

1,3-thiazolidine (504-78-9) + N-tert-butoxycarbonyl-4-oxo-L-proline (84348-37-8) → (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester (401564-36-1)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 2 - 7 ℃; for 2h; Large scale;

upstream raw materials:

3-[(2S,4R)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl]-1,3-thiazolidine

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

sodium hydrogencarbonate

1,3-thiazolidine

Downstream raw materials:

3-[(2S,4S)-4-(p-anisidino)-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl]-1,3-thiazolidine

3-((2S,4S)-4-anilino-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl)-1,3-thiazolidine

Refernces

• 1、 -. "Method for synthesizing tert-2-(3- (2S)-4- butyl)-1- ester of n-oxo-isothiazole alkyloxycarbonylpyrrolidinecarboxylic acid (by machine translation)". . . Retrieved 2020/02/14.
• 2、 -. "Industrial production method of teneligptin intermediate". Paragraph 0023; 0029-0034; 0040-0045; 0051-0056; 0062-0066. . Retrieved 2019/04/04.