Methanesulfonyl chloride → (2S,4R)-N-methanesulfonyl-4-hydroxyproline ethyl ester

HRID 1638403Notes

Reaction equation

HRID 1638403 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:12])[C@@H:6]1[CH2:10][C@@H:9]([OH:11])[CH2:8][NH:7]1)[CH3:3].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH2:2]([O:4][C:5](=[O:12])[C@@H:6]1[CH2:10][C@@H:9]([OH:11])[CH2:8][N:7]1[S:14]([CH3:13])(=[O:16])=[O:15])[CH3:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 12709304Ethyl trans-4-hydroxy-L-prolinate hydrochloride

Product 1

HCID 13665129(2S,4R)-N-methanesulfonyl-4-hydroxyproline ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 200 ml of pyridine was placed 19.56 g (0.1 mol) of (2S,4R)-4-hydroxyproline ethyl ester hydrochloride, and 12.03 g (0.105 mol) of methanesulfonyl chloride was slowly added dropwise to the mixture under agitation and ice-cooling. After stirring the mixture under ice-cooling for 6 hours, the mixture was further stirred overnight at room temperature. After distilling off the pyridine under reduced pressure, 10% hydrochloric acid was added to the reaction mixture under ice-cooling. The mixture was extracted three times with 200 ml of ethyl acetate in each case and the ethyl acetate extracts were combined, washed with 40 ml of a saturated aqueous solution of sodium chloride and then dried over magnesium sulfate. The extract was concentrated under reduced pressure and dried until dryness whereby a solid substance having a melting point of 111°-113° C. was obtained in a yield of 18.7 g (78.9%) which, after recrystallization from ethyl acetate, showed a melting point of 118°-120° C.

Workup

  1. additionwas slowly added dropwise to the mixture under agitation and ice-
  2. temperaturecooling
  3. temperaturecooling for 6 hours
  4. stirringthe mixture was further stirred overnight at room temperature
  5. distillationAfter distilling off the pyridine under reduced pressure, 10% hydrochloric acid
  6. additionwas added to the reaction mixture under ice-
  7. temperaturecooling
  8. extractionThe mixture was extracted three times with 200 ml of ethyl acetate in each case
  9. washwashed with 40 ml of a saturated aqueous solution of sodium chloride
  10. dry with materialdried over magnesium sulfate
  11. concentrationThe extract was concentrated under reduced pressure
  12. customdried until dryness whereby a solid substance
  13. customwas obtained in a yield of 18.7 g (78.9%) which
  14. customafter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-a1a890fc097a41fc8dddb5dff1595f0b
Source dataset
uspto-grants-1989_11
Patent number
US04879389

Reaction notes

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