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

HRID 1746340Notes

Reaction equation

HRID 1746340 reaction equation
[CH3:1]O.S(Cl)([Cl:5])=O.[NH2:7][C@@H:8]([C:16]([OH:18])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[ClH:5].[CH3:1][O:17][C:16](=[O:18])[C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 71567D-Phenylalanine

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a chilled solution of methanol (1000 ml), was charged thionyl chloride (100 ml, 1.361 moles) at 5° C.±3° C. under nitrogen atmosphere. D-Phenyl alanine (100 grams, 0.602 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 form a residue. The residue was stirred in toluene (500 ml). The solid was isolated by filtration, washed with toluene (2×500 ml) and dried at 50-55° C. under vacuum to yield the desired product.

Workup

  1. stirringThe reaction mass was further stirred for 12 hours
  2. concentrationconcentrated at 50° C. under reduced pressure
  3. customto form a residue
  4. customThe solid was isolated by filtration
  5. washwashed with toluene (2×500 ml)
  6. customdried at 50-55° C. under vacuum

Sources & evidence

ORD record
ord-5299383a0dfc47c19e4bc7d4cbb13361
Source dataset
uspto-grants-2015_10
Patent number
US09150499B2

Reaction notes

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