4-Toluenesulfonyl chloride → 1-(4-Toluenesulfonyl)-4-hydroxy-D-proline

HRID 1087624Notes

Reaction equation

HRID 1087624 reaction equation
[OH:1][CH:2]1[CH2:6][NH:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([N:5]2[CH2:6][CH:2]([OH:1])[CH2:3][C@@H:4]2[C:7]([OH:9])=[O:8])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 5318330(2R)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 186462661-(4-Toluenesulfonyl)-4-hydroxy-D-prolineYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 g (76.30 mmol) of 4-hydroxy-D-proline in 75 ml of water was added 17.45 g (91.6 mmol) of 4-toluenesulfonyl chloride and 17 g (160.2 mmol) of sodium carbonate and the mixture was allowed to stir for 24 hours at room temperature. The reaction was then acidified to pH 1 by the careful addition of 10% aqueous HC1 solution and the product was isolated by filtration. After drying at high vacuum, 18.5 g of product was isolated (85% yield). M.P.=145°-146° C.

Workup

  1. additionThe reaction was then acidified to pH 1 by the careful addition of 10% aqueous HC1 solution
  2. customthe product was isolated by filtration
  3. customAfter drying at high vacuum

Sources & evidence

ORD record
ord-4b75f4f36c8d4ed79ccc053d69eced39
Source dataset
uspto-grants-1991_07
Patent number
US05036153

Reaction notes

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