Hydrochloric Acid → (2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acid

HRID 1976236Notes

Reaction equation

HRID 1976236 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[OH-].[Na+].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.Cl>>[S:17]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 145742L-Proline

Product 1

HCID 691957(2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acidYield 98.3%

Conditions

Temperature
70 °C

Procedure

To a solution of 7 g of L-proline in 120 ml of a 2N aqueous sodium hydroxide solution, there was added 11.8 g of p-toluenesulfonyl chloride and the mixture was heated to 70° C. for one hour with stirring. After the reaction solution was ice-cooled, it was acidified with hydrochloric acid and then extracted with ethyl acetate. The resulting organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated to give 16.1 g (yield 98.3%) of the title compound.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ab5a3bf461854056a46463d94ad6d5e6
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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