Hydrochloric Acid → (2S)-2-amino-2-phenylpropanoic acid hydrochloride

HRID 605413Notes

Reaction equation

HRID 605413 reaction equation
C([NH:3][C@:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[C:5]([OH:7])=[O:6])=O.[ClH:15]>>[ClH:15].[NH2:3][C@:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86615567HCID 86615567, compound

Product 1

HCID 67040491(2S)-2-amino-2-phenylpropanoic acid hydrochloride

Procedure

The product of Example 445B (1.25g, 7.6 mmol)) in 1N HCl (12.5 mL) was refluxed for 1 hour. The reaction mixture was concentrated and dried at 40° C. under vacuum overnight to give (S)-2-amino-2-phenylpropanoic acid hydrochloride as a pale brown crystal (1.53 g). The intermediate amino acid (1.5 g. 7.5 mmol) was dissolved in EtOH (30 mL) was reacted with thionyl chloride (2.7 ml., 37.5 mmol) dropwise at room temperature then refluxed for 23 hours. The reaction was concentrated and the residue was partitioned between saturated NaHCO3 solution and ethyl acetate. The organic layer was washed with water (3×15 mL) and 10% aqueous NaHCO3 (1×15 mL), dried over MgSO4, concentrated to give the title compound (1.28 g, 90%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried at 40° C. under vacuum overnight

Sources & evidence

ORD record
ord-189cfdd2f6bd4bc8b245964173925237
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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