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

HRID 1746342Notes

Reaction equation

HRID 1746342 reaction equation
S(Cl)([Cl:3])=O.[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.N.[CH3:18]O>>[ClH:3].[CH3:18][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

5

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 24386Thionyl ChlorideHCID 71567D-Phenylalanine

Product 1

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

Conditions

Temperature
25 °C

Procedure

To a chilled solution of methanol (500 ml), was charged thionyl Chloride (50 ml, 0.681 moles) at 5° C.±3° C. under nitrogen atmosphere. D-Phenyl alanine (50 grams, 0.301 moles) was added at 5° C.±3° C. and further stirred for 30 minutes. The temperature was raised to 25° C. The reaction mass was further stirred for 12 hours and concentrated at 50° C. under reduced pressure to obtain residue. Basified with aqueous ammonia, extracted with dichloromethane (250 ml×2), dried over sodium sulphate and concentrated to obtain D-phenyl alanine methyl ester hydrochloride.

Workup

  1. stirringThe reaction mass was further stirred for 12 hours
  2. concentrationconcentrated at 50° C. under reduced pressure
  3. customto obtain residue
  4. extractionextracted with dichloromethane (250 ml×2)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f41826fb7d3f4213b31f3dbf0110a81f
Source dataset
uspto-grants-2015_10
Patent number
US09150499B2

Reaction notes

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