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

HRID 1879322Notes

Reaction equation

HRID 1879322 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

5

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6329MethylamineHCID 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.

Workup

  1. customthe temperature below 30° C.
  2. extractionextracted several times with dichloromethane
  3. customthe water is removed by azeotropic distillation

Sources & evidence

ORD record
ord-bb0ea9efbb0243278b8fc916ca2e5970
Source dataset
uspto-grants-2012_11
Patent number
US08314238B2

Reaction notes

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