Acetyl chloride → methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride

HRID 589265Notes

Reaction equation

HRID 589265 reaction equation
[C:1]([Cl:4])(=O)C.[NH2:5][C@@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[ClH:4].[CH3:1][O:15][C:14](=[O:16])[C@@H:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:5]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 71567D-Phenylalanine

Product 1

HCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Anhydrous methanol (50 mL) is taken in a 100 mL 2-necked round bottom flask fitted with a reflux condenser and an additional dropping funnel and cooled to ice temperature. Acetyl chloride (3 mL) is added drop wise through the dropping funnel. After 15 min, D-phenylalanine (3 g, 18.16 mmol) is added and the reaction mixture is refluxed at 70° C. for overnight. The reaction mixture is vacuo dried to obtain D-phenylalanine methylester hydrochloride in quantitative yield and used for further reaction without purification.

Workup

  1. customfitted with a reflux condenser and an additional dropping funnel
  2. temperaturecooled to ice temperature
  3. customdried

Sources & evidence

ORD record
ord-6df0025dd8ac4f0ca677d8cd9cc13762
Source dataset
uspto-grants-2016_01
Patent number
US09230708B2

Reaction notes

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