4-Toluenesulfonyl chloride → HCID 57114913, compound

HRID 744887Notes

Reaction equation

HRID 744887 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[CH2:10][C@H:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12709318HCID 12709318, compound

Product 1

HCID 57114913HCID 57114913, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 193 g of (2S,4R)-1-(t-butoxycarbonyl)-2-ethoxycarbonyl -4-hydroxypyrrolidine dissolved in 500 ml of pyridine and cooled on an ice bath was added 213 g of p-toluenesulfonyl chloride, followed by 20 hours of stirring at room temperature. The reaction mixture was concentrated, and the resulting residue was dissolved in ethyl acetate, washed with water, 10% citric acid aqueous solution, 5% sodium bicarbonate aqueous solution and water in that order, followed by evaporation of the solvent under a reduced pressure to yield 289 g of (2S,4R)-1-(t-butoxycarbonyl)-2-ethoxycarbonyl-4-(p-toluenesulfonyloxy)pyrrolidine.

Workup

  1. temperaturecooled on an ice bath
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe resulting residue was dissolved in ethyl acetate
  4. washwashed with water, 10% citric acid aqueous solution, 5% sodium bicarbonate aqueous solution and water in that order
  5. customfollowed by evaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-cdf36983eb5d4d0f9e57b0e9ef48f548
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

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