(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate

Base Information

• Chemical Name: (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate
• CAS No.: 51693-17-5
• Molecular Formula: C12H15NO4S
• Molecular Weight: 269.321
• Hs Code.: 29339980
• European Community (EC) Number: 626-809-4
• DSSTox Substance ID: DTXSID80965966
• Nikkaji Number: J820.694E
• Mol file: 51693-17-5.mol

Synonyms:51693-17-5;(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate;(S)-(5-oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate;[(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzenesulfonate;2-Pyrrolidinone, 5-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, (5S)-;[(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonate;MFCD00274229;(S)-(+)-5-(hydroxymethyl)-2-pyrrolidinone P-tolu;SCHEMBL344917;DTXSID80965966;AMZNHHZJURKRFX-JTQLQIEISA-N;BCA69317;toluene-4-sulfonic acid (S)-5-oxo-pyrrolidin-2-ylmethyl ester;5beta-(Tosyloxymethyl)pyrrolidin-2-one;s11128;CS-0068961;EN300-7345178;(S)-(5-oxopyrrolidin-2-yl)methyl-4-methylbenzenesulfonate;(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone ptoluenesulfonate;(S)-toluene4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester;toluene-4-sulphonic acid-(S)-5-oxo-pyrrolidin-2-ylmethyl ester;(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate, 95%;toluene-4-sulfonic acid [(S)-5-oxopyrrolidin-2-yl]methyl ester;(5-Hydroxy-3,4-dihydro-2H-pyrrol-2-yl)methyl 4-methylbenzene-1-sulfonate

Chemical Property of (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate

Chemical Property:

• Appearance/Colour: colorless to beige powder
• Vapor Pressure: 2.58E-10mmHg at 25°C
• Melting Point: 124-128 °C(lit.)
• Refractive Index: 1.545
• Boiling Point: 504.8 °C at 760 mmHg
• PKA: 15.34±0.40(Predicted)
• Flash Point: 259.1 °C
• PSA: 80.85000
• Density: 1.275 g/cm³
• LogP: 2.38850
• Storage Temp.: Refrigerator (+4°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:

98%,99%, ^*data from raw suppliers

(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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
• Uses: Serves as a building block in the synthesis of (R)- and (S)-diaminovaleric acids and of 5-azasemicorrin bidentate nitrogen ligands for enantioselective catalysis.

Technology Process of (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate

There total 11 articles about (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate 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) + L-Pyroglutamic acid (98-79-3) → (S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester (51693-17-5)

Guidance literature:

L-Pyroglutamic 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: 98.0%

p-toluenesulfonyl chloride (98-59-9) + (S)-Pyroglutaminol (17342-08-4) → (S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester (51693-17-5)

Guidance literature:

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

DOI:10.1021/jo0506682

Reference yield:

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + p-toluenesulfonyl chloride (98-59-9) + ethyl (S)-pyroglutamate (7149-65-7) → (S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester (51693-17-5)

Guidance literature:

With sodium borohydrid; In dichloromethane; water; acetone;

upstream raw materials:

p-toluenesulfonyl chloride

(S)-Pyroglutaminol

ethyl (S)-pyroglutamate

methyl (S)-pyroglutamate

Downstream raw materials:

(S)-1-acetyl-5-iodomethyl-pyrrolidin-2-one

2-[(2S)-5-oxopyrrolidin-2-yl]acetonitrile

(S)-5-biphenyl-4-ylmethylpyrrolidin-2-one

N-[(2Z)-5-tert-butyl-3-{[(2S)-5-oxopyrrolidin-2-yl]methyl}-1,3-thiazol-2(3H)-ylidene]-5-chloro-2-methoxybenzamide

Refernces

• 1、 Catlin, Daniel S.,Reidl, Cory T.,Trzupek, Thomas R.,Silverman, Richard B.,Cannon, Brian L.,Becker, Daniel P.,Liu, Dali. "(S)-4-Amino-5-phenoxypentanoate designed as a potential selective agonist of the bacterial transcription factor GabR". . p. 1816 - 1828. Retrieved 2020.
• 2、 -. "NOVEL FUNCTIONALIZED LACTAMS AS MODULATORS OF THE 5-HYDROXYTRYPTAMINE RECEPTOR 7 AND THEIR METHOD OF USE". Paragraph 000723-000724. . Retrieved 2021/05/21.