1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 2-methyl 1-(phenylmethyl) ester, (2S,4R)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 2-methyl 1-(phenylmethyl) ester, (2S,4R)-
• CAS No.: 57653-38-0
• Molecular Formula: C21H23NO7S
• Molecular Weight: 433.482
• Mol file: 57653-38-0.mol

Synonyms:

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 2-methyl 1-(phenylmethyl) ester, (2S,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 2-methyl 1-(phenylmethyl) ester, (2S,4R)-

There total 7 articles about 1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 2-methyl 1-(phenylmethyl) ester, (2S,4R)- 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: 97.0%

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) + N-tosylimidazole (2232-08-8) → N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester (57653-38-0)

Guidance literature:

With 1-methyl-1H-imidazole; methyl trifluoromethanesulfonate; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2005.11.058

Reference yield: 96.2%

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) + p-toluenesulfonyl chloride (98-59-9) → N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester (57653-38-0)

Guidance literature:

With pyridine; In 1,2-dimethoxyethane; at 5 - 25 ℃; for 1h;

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester (57653-38-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / sodium bicarbonate / H₂O; dioxane / 23 h / 0 - 20 °C

2: 63 percent / pyridine / 22 h / 4 °C

With sodium hydrogencarbonate; In 1,4-dioxane; pyridine; water;

DOI:10.1021/ja010812a

upstream raw materials:

diazomethane

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

p-toluenesulfonyl chloride

Downstream raw materials:

cis-4-methylsulfanyl-L-proline

(2S,4R)-1-[(benzyloxy)carbonyl]-4-(p-toluenesulfonyloxy)pyrrolidine-2-formic acid

(4R)-N-benzyloxycarbonyl-4-(4-toluenesulfonyloxy)-L-prolyl chloride

C₁₃H₁₈N₂O₃

Refernces

• 1、 -. "A inhibiting DPP-IV compounds and intermediates". Paragraph 0206-0209. . Retrieved 2016/10/20.
• 2、 Gardelli, Cristina,Nizi, Emanuela,Muraglia, Ester,Crescenzi, Benedetta,Ferrara, Marco,Orvieto, Federica,Pace, Paola,Pescatore, Giovanna,Poma, Marco,Ferreira, Maria Del Rosario Rico,Scarpelli, Rita,Homnick, Carl F.,Ikemoto, Norihiro,Alfieri, Anna,Verdirame, Maria,Bonelli, Fabio,Paz, Odalys Gonzalez,Taliani, Marina,Monteagudo, Edith,Pesci, Silvia,Laufer, Ralph,Felock, Peter,Stillmock, Kara A.,Hazuda, Daria,Rowley, Michael,Summa, Vincenzo. "Discovery and synthesis of HIV integrase inhibitors: Development of potent and orally bioavailable N-methyl pyrimidones". . p. 4953 - 4975. Retrieved 2008/03/14.