Dichloromethane → (S)-2-(Methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonate

HRID 888003Notes

Reaction equation

HRID 888003 reaction equation
[C:1]([NH2:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[OH-].[Na+].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.Cl[CH2:26]Cl>>[CH3:26][NH:11][C:1]([C@@H:2]([O:3][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:10]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 73558Mandelamide

Product 1

HCID 57354974(S)-2-(Methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonate

Procedure

Alternatively, to the solution of mandelic acid amide in dichloromethane is added 50% aqueous caustic soda at RT. Subsequently p-toluene sulfonic acid chloride (1.0 equivalent) is added as a solution in dichloromethane keeping the temperature below 25° C. The biphasic reaction mixture is stirred at RT until a satisfactory conversion is reached, phases are separated, the aqueous phase is extracted once with dichloromethane and then the combined organic phases are washed with water. After a solvent switch to toluene the solution is concentrated, cooled to 5° C. and the precipitate filtered. The crystals are washed with cooled toluene and dried in vacuo at 40° C.

Workup

  1. customThe biphasic reaction mixture
  2. customphases are separated
  3. extractionthe aqueous phase is extracted once with dichloromethane
  4. washthe combined organic phases are washed with water
  5. concentrationAfter a solvent switch to toluene the solution is concentrated
  6. temperaturecooled to 5° C.
  7. filtrationthe precipitate filtered
  8. washThe crystals are washed with cooled toluene
  9. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-8232494920ad4da7a07219ed6f3c8deb
Source dataset
uspto-grants-2012_08
Patent number
US08247560B2

Reaction notes

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