Methanol → Methyl 2-amino-3-(3,5-difluorophenyl)propanoate hydrochloride

HRID 714280Notes

Reaction equation

HRID 714280 reaction equation
[CH:1]1[C:6]([F:7])=[CH:5][C:4]([F:8])=[CH:3][C:2]=1[CH2:9][CH:10]([NH2:14])[C:11]([OH:13])=[O:12].S(Cl)([Cl:17])=O.[CH3:19]O>>[ClH:17].[NH2:14][CH:10]([CH2:9][C:2]1[CH:3]=[C:4]([F:8])[CH:5]=[C:6]([F:7])[CH:1]=1)[C:11]([O:13][CH3:19])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27370453,5-Difluorophenylalanine

Product 1

HCID 66940454Methyl 2-amino-3-(3,5-difluorophenyl)propanoate hydrochlorideYield 98%

Procedure

To a stirred suspension of DL-3,5-difluorophenylalanine (3.00 g, 14.9 mmol) in anhydrous methanol (30 mL) was added dropwise thionyl chloride (1.64 mL, 22.5 mmol) at 0° C. The resulting solution was refluxed for 18 hours, cooled to ambient temperature and concentrated in vacuo to dryness. The residue was triturated with diethyl ether to give methyl 2-amino-3-(3,5-difluorophenyl)propanoate hydrochloride as a colorless crystalline solid (3.68 g, 98%): 1H NMR (300 MHz, CD3OD) δ 6.93-6.84 (m, 3H), 4.34 (dd, J=7.4, 6.3 Hz, 1H), 3.78 (s, 3H), 3.30-3.09 (m, 2H).

Workup

  1. temperatureThe resulting solution was refluxed for 18 hours
  2. concentrationconcentrated in vacuo to dryness
  3. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-964e5df672324b5ba85f6638108567f1
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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