1-(Benzenesulfonyl)-L-prolyl chloride

Base Information

• Chemical Name: 1-(Benzenesulfonyl)-L-prolyl chloride
• CAS No.: 72922-83-9
• Molecular Formula: C11H12ClNO3S
• Molecular Weight: 273.74
• DSSTox Substance ID: DTXSID80502113
• Nikkaji Number: J1.240.997D
• Wikidata: Q82354906
• Mol file: 72922-83-9.mol

Synonyms:72922-83-9;1-(Benzenesulfonyl)-L-prolyl chloride;DTXSID80502113

Chemical Property of 1-(Benzenesulfonyl)-L-prolyl chloride

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 273.0226421
• Heavy Atom Count: 17
• Complexity: 384

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)S(=O)(=O)C2=CC=CC=C2)C(=O)Cl
• Isomeric SMILES: C1C[C@H](N(C1)S(=O)(=O)C2=CC=CC=C2)C(=O)Cl

Technology Process of 1-(Benzenesulfonyl)-L-prolyl chloride

There total 8 articles about 1-(Benzenesulfonyl)-L-prolyl chloride 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: 62.0%

N-benzenesulfonyl-L-proline (88425-46-1) → (S)‐1‐(phenylsulfonyl)pyrrolidine‐2‐carbonyl chloride (72922-83-9)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/ja00316a047

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (S)‐1‐(phenylsulfonyl)pyrrolidine‐2‐carbonyl chloride (72922-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / aq. NaOH / 5 h / Ambient temperature

2: 62 percent / oxalyl chloride, DMF / CH₂Cl₂ / 1 h / Ambient temperature

With oxalyl dichloride; N,N-dimethyl-formamide; In sodium hydroxide; dichloromethane;

DOI:10.1021/ja00316a047

Reference yield:

L-(phenylsulfonyl)proline (88425-46-1) → (S)‐1‐(phenylsulfonyl)pyrrolidine‐2‐carbonyl chloride (72922-83-9)

Guidance literature:

With thionyl chloride; In benzene; at 35 - 40 ℃; for 48h;

DOI:10.1021/ac00270a022

upstream raw materials:

N-benzenesulfonyl-L-proline

L-(phenylsulfonyl)proline

benzenesulfonyl chloride

L-proline

Downstream raw materials:

2-(S)-1-benzenesulfonylpyrrolidine-2-carbonitrile

3-(1-benzenesulfonylpyrrolidin-2-yl)-1,2,4-oxadiazole

5-methyl-3-(1-benzenesulfonylpyrrolidin-2-yl)-1,2,4-oxadiazole

5-phenyl-3-(1-benzenesulfonylpyrrolidin-2-yl)-1,2,4-oxadiazole

Refernces

• 1、 Oila, Markku J.,Tois, Jan E.,Koskinen, Ari M.P.. "Ligand creation via linking - A rapid and convenient method for construction of novel supported PyOX-ligands". . p. 10748 - 10756. Retrieved 2007/10/03.
• 2、 Itoh, Takashi,Matsuya, Y?ji,Enomoto, Yasuko,Ohsawa, Akio. "Preparation of both enantiomers of 1-allyl-1,2,3,4-tetrahydro-β-carboline using allyltin reagents and a chiral auxiliary derived from L-proline". . p. 7277 - 7289. Retrieved 2007/10/03.