4-Toluenesulfonyl chloride → HCID 14830188, compound

HRID 1088253Notes

Reaction equation

HRID 1088253 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:26][OH:27])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>N1C=CC=CC=1.O>[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:26][O:27][S:36]([C:33]2[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=2)(=[O:38])=[O:37])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 14830186HCID 14830186, compound

Product 1

HCID 14830188HCID 14830188, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

(2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-2-hydroxymethyl-4-benzoyloxypyrrolidine (32.6 g) was dissolved in 64 ml of dry pyridine, and 28.02 g of p-toluenesulfonyl chloride was added thereto, followed by stirring at room temperature for 12 hours. The reaction mixture was diluted with water and extracted with a mixture of diethyl ether and dichloromethane (4:1). The extract was washed successively with brine, dilute hydrochloric acid, brine, a saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and distilled to remove the solvent. Recrystallization of the residue from diethyl ether gave (2S,4R)-1-(p-nitrobenzyloxycarbonyl)-2-p-toluenesulfonyloxymethyl-4-benzoyloxypyrrolidine.

Workup

  1. extractionextracted with a mixture of diethyl ether and dichloromethane (4:1)
  2. washThe extract was washed successively with brine, dilute hydrochloric acid, brine
  3. dry with materiala saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customRecrystallization of the residue from diethyl ether

Sources & evidence

ORD record
ord-212533dbeeaf4674a2b4b7a6ec06f5f4
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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