L-Hydroxyproline → 1-(4-Toluenesulfonyl)-4-hydroxy-D-proline

HRID 2166926Notes

Reaction equation

HRID 2166926 reaction equation
[OH:1][C@H: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>[OH-].[Na+].CCOCC>[OH:1][CH:2]1[CH2:6][N:5]([S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1

Participants

5

Reactant 2

HCID 5810L-HydroxyprolineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 186462661-(4-Toluenesulfonyl)-4-hydroxy-D-prolineYield 93.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
5 °C

Procedure

A stirred solution of 52.45 g (0.40 mole) of trans-4-hydroxy-L-proline in 500 ml of sodium hydroxide is treated with 85.79 g (0.45 mole) of p-toluenesulfonyl chloride in 500 ml of ether at room temperature. Stirring is continued for 6 hours, the layers are separated and the aqueous phase is cooled to 5° C. in an ice-bath. The mixture is then acidified while cooling with 30 ml of concentrated hydrochloric acid to pH 2 and the precipitated white solid is collected, washed with 150 ml of cold water, and dried in vacuo yielding 106.2 g of material, melting point 139°-143° C. Crystallization from 300 ml of ethyl acetate yields 98.6 g of the title compound, melting point 142°-145° C.

Workup

  1. customthe layers are separated
  2. temperaturewhile cooling with 30 ml of concentrated hydrochloric acid to pH 2
  3. customthe precipitated white solid is collected
  4. washwashed with 150 ml of cold water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a079e14f76734164a9caa4af22cd6999
Source dataset
uspto-grants-1983_06
Patent number
US04390695

Reaction notes

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