(2R, 4R)-4-(TOLUENE-4-SULFONYLOXY)-1-[BENZYLOXYCARBONYL]-PYRROLIDINE-2-ETHYLCARBOXYLATE

Base Information

• Chemical Name: (2R, 4R)-4-(TOLUENE-4-SULFONYLOXY)-1-[BENZYLOXYCARBONYL]-PYRROLIDINE-2-ETHYLCARBOXYLATE
• CAS No.: 130830-60-3
• Molecular Formula: C22H25 N O7 S
• Molecular Weight: 447.509
• Mol file: 130830-60-3.mol

Synonyms:(2R, 4R)-4-(TOLUENE-4-SULFONYLOXY)-1-[BENZYLOXYCARBONYL]-PYRROLIDINE-2-ETHYLCARBOXYLATE

Chemical Property of (2R, 4R)-4-(TOLUENE-4-SULFONYLOXY)-1-[BENZYLOXYCARBONYL]-PYRROLIDINE-2-ETHYLCARBOXYLATE

Chemical Property:

• PSA: 107.59000
• LogP: 4.06180

Purity/Quality:

99%min ^*data from raw suppliers

(2R,4R)-4-(TOLUENE-4-SULFONYLOXY)-1-[BENZYLOXYCARBONYL]PYRROLIDINE-2-ETHYLCARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R, 4R)-4-(TOLUENE-4-SULFONYLOXY)-1-[BENZYLOXYCARBONYL]-PYRROLIDINE-2-ETHYLCARBOXYLATE

There total 5 articles about (2R, 4R)-4-(TOLUENE-4-SULFONYLOXY)-1-[BENZYLOXYCARBONYL]-PYRROLIDINE-2-ETHYLCARBOXYLATE 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%

(2S,4R)-ethyl N1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate (103667-57-8) + p-toluenesulfonyl chloride (98-59-9) → 1-benzyl 2-ethyl(2S,4R)-4-[[(4-methylbenzene)sulfonyl]oxy]pyrrolidine-1,2-dicarboxylate (130830-60-3)

Guidance literature:

With pyridine; In chloroform; for 72h; Ambient temperature;

DOI:10.1021/jm00106a037

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → 1-benzyl 2-ethyl(2S,4R)-4-[[(4-methylbenzene)sulfonyl]oxy]pyrrolidine-1,2-dicarboxylate (130830-60-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / NaHCO₃ / H₂O; toluene / 16 h / Ambient temperature

2: 100 percent / p-toluenesulfonic acid / ethanol / 16 h / Heating

3: 98 percent / pyridine / CHCl₃ / 72 h / Ambient temperature

With pyridine; sodium hydrogencarbonate; toluene-4-sulfonic acid; In ethanol; chloroform; water; toluene;

DOI:10.1021/jm00106a037

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 1-benzyl 2-ethyl(2S,4R)-4-[[(4-methylbenzene)sulfonyl]oxy]pyrrolidine-1,2-dicarboxylate (130830-60-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / NaHCO₃ / H₂O; toluene / 16 h / Ambient temperature

2: 100 percent / p-toluenesulfonic acid / ethanol / 16 h / Heating

3: 98 percent / pyridine / CHCl₃ / 72 h / Ambient temperature

With pyridine; sodium hydrogencarbonate; toluene-4-sulfonic acid; In ethanol; chloroform; water; toluene;

DOI:10.1021/jm00106a037

upstream raw materials:

(2S,4R)-ethyl N¹-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate

p-toluenesulfonyl chloride

benzyl chloroformate

4R-4-hydroxyproline

Downstream raw materials:

cis-N-(benzyloxycarbonyl)-4-carboxy-L-proline methyl ester

C₁₅H₁₉NO₅

C₂₁H₂₃NO₄

C₂₈H₂₉NO₄

Refernces

• 1、 -. "HETEROCYCLIC COMPOUNDS AND METHODS FOR THEIR USE". Page/Page column 160. . Retrieved 2013/07/19.