Hydrochloric Acid → (S)-(+)-Mandelamide

Reaction equation

C[NH2:2].[C:3]([O:13]C)(=O)[C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].Cl.[Cl-].[Na+]>>[C:3]([NH2:2])(=[O:13])[C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 5234Sodium Chloride

HCID 6329Methylamine

HCID 643570methyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 818990(S)-(+)-Mandelamide

Procedure

To a solution of methylamine (40% in water, 3.8 equivalents) is added, at ambient temperature, methyl (S)-mandelate (1.0 equivalent; commercially available), while keeping the temperature below 30° C. and stirred at ambient temperature until full conversion is achieved. After neutralisation with aqueous hydrochloric acid the aqueous solution is saturated with sodium chloride and extracted several times with dichloromethane. The organic layers are combined and the water is removed by azeotropic distillation.