METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE

Base Information

• Chemical Name: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE
• CAS No.: 16257-57-1
• Molecular Formula: C13H17NO5S
• Molecular Weight: 299.348
• Hs Code.: 2933990090
• Mol file: 16257-57-1.mol

Synonyms:L-Proline,4-hydroxy-1-[(4-methylphenyl)sulfonyl]-, methyl ester, trans-;Proline,4-hydroxy-1-(p-tolylsulfonyl)-, methyl ester (7CI);Proline,4-hydroxy-1-(p-tolylsulfonyl)-, methyl ester, L-trans- (8CI);

Chemical Property of METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE

Chemical Property:

• Vapor Pressure: 4.43E-09mmHg at 25°C
• Melting Point: 97-99 °C
• Refractive Index: 1.586
• Boiling Point: 455.3 °C at 760 mmHg
• PKA: 13.88±0.40(Predicted)
• Flash Point: 229.1 °C
• PSA: 92.29000
• Density: 1.373 g/cm³
• LogP: 1.31060
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Methyl 4-hydroxy-1-[(4-methylphenyl)sulfonyl]-2-pyrrolidinecarboxylate >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE

There total 9 articles about METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-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: 98.0%

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) + p-toluenesulfonyl chloride (98-59-9) → methyl (2S,4R)-4-hydroxy-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate (16257-57-1)

Guidance literature:

With triethylamine; In dichloromethane; for 10h; cooling;

DOI:10.3987/COM-05-10407

Reference yield: 84.0%

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) + p-toluenesulfonyl chloride (98-59-9) → methyl (2S,4R)-4-hydroxy-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate (16257-57-1) + N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester (16257-73-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → methyl (2S,4R)-4-hydroxy-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate (16257-57-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / thionyl chloride / 4.17 h

2: 98 percent / triethylamine / CH₂Cl₂ / 10 h / cooling

With thionyl chloride; triethylamine; In dichloromethane;

DOI:10.3987/COM-05-10407

upstream raw materials:

methanol

N--trans-4-hydroxy-L-proline

L-4-hydroxyproline methyl ester hydrochloride

p-toluenesulfonyl chloride

Downstream raw materials:

N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester

methyl N-toluenesulfonyl-O-t-butyldimethylsilyl-4-hydroxyprolinate

(2S)-1-(4-methylphenylsulfonyl)-2-vinylpyrrolidin-4-one

(2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine