Hydrochloric Acid → 1-(4-Toluenesulfonyl)-4-hydroxy-L-proline

HRID 1614341Notes

Reaction equation

HRID 1614341 reaction equation
[OH:1][CH:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>O>[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([N:5]2[CH2:6][CH:2]([OH:1])[CH2:3][C@H:4]2[C:7]([OH:9])=[O:8])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 69248L-Proline, 4-hydroxy-, cis-

Product 1

HCID 211404091-(4-Toluenesulfonyl)-4-hydroxy-L-prolineYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 100 g (763 mmol) of 4-hydroxy-L-proline in 750 ml of water was added 169.9 g (1602 mmol) of sodium carbonate at 0° C. along with 174.5 g (916 mmol) of 4-toluenesulfonyl chloride (added in 3 portions over a period of 1 hour). The slurry was then warmed to room temperature and allowed to stir for 48 hours. The reaction was acidified with concentrated hydrogen chloride solution to pH 2 and the product was isolated via filtration. The filter cake was washed with pH 2 buffer and dried in a vacuum oven at 60° C. for 16 hours to obtain 215.3 g of the product as a white crystalline solid in 99% yield. M.P.=149°-151° C.

Workup

  1. additionadded in 3 portions over a period of 1 hour)
  2. customthe product was isolated via filtration
  3. washThe filter cake was washed with pH 2 buffer
  4. customdried in a vacuum oven at 60° C. for 16 hours

Sources & evidence

ORD record
ord-c2a63a7cb2e84ee88f61e7693bf6cc08
Source dataset
uspto-grants-1993_03
Patent number
US05196548

Reaction notes

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