Oxalyl chloride → (S)-N-(2-naphthalenesulfonyl)prolyl chloride

HRID 1285227Notes

Reaction equation

HRID 1285227 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[C:19]([OH:21])=O)(=[O:13])=[O:12].C(Cl)(=O)C([Cl:25])=O>C1C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[C:19]([Cl:25])=[O:21])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 804321(S)-1-(Naphthalen-2-ylsulfonyl)pyrrolidine-2-carboxylic acid

Product 1

HCID 13576782(S)-N-(2-naphthalenesulfonyl)prolyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

15.6 g of (S)-1-(2-naphthylsulfonyl)pyrrolidine-2-carboxylic acid [Chem, Ber., 35, 3783 (1902)] are dissolved in 120 ml of anhydrous benzene, and 17.5 ml of oxalyl dichloride are added dropwise thereto under stirring. The mixture is allowed to stand at 40° to 50° C. overnight. Then, the mixture is condensed to dryness under reduced pressure, and the residue is recrystallized from a mixture of n-hexane and benzene. 14.3 g of (S)-1-(2-naphthylsulfonyl)pyrrolidine-2-carbonyl chloride are obtained.

Workup

  1. customcondensed to dryness under reduced pressure
  2. customthe residue is recrystallized from a mixture of n-hexane and benzene

Sources & evidence

ORD record
ord-daf7465b75dd4f40b7e556089f4f3802
Source dataset
uspto-grants-1986_01
Patent number
US04565877

Reaction notes

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