(R)-(5-Oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (R)-(5-Oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate
• CAS No.: 128899-31-0
• Molecular Formula: C12H15NO4S
• Molecular Weight: 269.321
• Hs Code.: 2933790090
• European Community (EC) Number: 839-838-4
• DSSTox Substance ID: DTXSID40536035
• Nikkaji Number: J3.422.778K
• Wikidata: Q82410541
• Mol file: 128899-31-0.mol

Synonyms:128899-31-0;(R)-(5-Oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate;[(2R)-5-Oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonate;[(2R)-5-OXOPYRROLIDIN-2-YL]METHYL 4-METHYLBENZENESULFONATE;2-Pyrrolidinone, 5-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (5R)-;(+)-D-PYROGLUTAMOL P-TOLUENESULFONATE;MFCD09864865;AMZNHHZJURKRFX-SNVBAGLBSA-N;SCHEMBL344733;DTXSID40536035;AKOS016014479;AS-72070;CS-0217424;EN300-7433516;(R)-(5-Oxopyrrolidin-2-yl)methyl4-methylbenzenesulfonate;(R)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester;toluene-4-sulfonic acid (R)-5-oxo-pyrrolidin-2-ylmethyl ester;toluene-4-sulfonic acid [(R)-5-oxopyrrolidin-2-yl]methyl ester

Chemical Property of (R)-(5-Oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate

Chemical Property:

• PSA: 84.34000
• LogP: 2.33560
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 269.07217913
• Heavy Atom Count: 18
• Complexity: 393

Purity/Quality:

99.3% ^*data from raw suppliers

(R)-(5-Oxopyrrolidin-2-yl)methyl4-methylbenzenesulfonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2CCC(=O)N2
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]2CCC(=O)N2

Technology Process of (R)-(5-Oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate

There total 7 articles about (R)-(5-Oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate 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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + D-pyrrolidone-5-carboxylic acid (4042-36-8) → <(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate (128899-31-0)

Guidance literature:

D-pyrrolidone-5-carboxylic acid; With thionyl chloride; In methanol; at 20 ℃; for 4h;

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 15h;

p-toluenesulfonyl chloride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.3987/COM-19-S(F)6

Reference yield: 95.0%

(R)-5-hydroxymethylpyrrolidin-2-one (66673-40-3) + p-toluenesulfonyl chloride (98-59-9) → <(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate (128899-31-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetasy.2008.10.006

Reference yield:

ethyl (R)-2-pyrrolidone-5-carboxylate (68766-96-1) → <(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate (128899-31-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.75 h / 50 °C

1.2: 20 °C / pH 3

2.1: triethylamine / dichloromethane / 0 - 20 °C

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

(R)-5-hydroxymethylpyrrolidin-2-one

p-toluenesulfonyl chloride

D-Glutamic acid

methyl (2R)-pyroglutamate

Downstream raw materials:

(R)-2-(5-oxopyrrolidin-2-yl)acetonitrile

(R)-5-(2-hydroxyethyl)pyrrolidin-2-one

(5R)-5-(bromomethyl)pyrrolidin-2-one

C₂₄H₂₃Cl₂N₇O₃

Refernces

• 1、 Yasuno, Yoko,Sawai, Akira,Sekihara, Ai,Shinada, Tetsuro. "Synthesis of optically active (R)- And (S)-β-arginine from pyroglutamic acid". . p. 165 - 176. Retrieved 2020/02/04.
• 2、 -. "HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF DISEASE". Paragraph 00217. . Retrieved 2017/06/01.