Methanol → Methyl L-phenylalaninate hydrochloride

HRID 2392825Notes

Reaction equation

HRID 2392825 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(Cl)([Cl:15])=O.[CH3:17]O>>[ClH:15].[CH3:17][O:11][C:10](=[O:12])[C@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 6140L-PhenylalanineHCID 24386Thionyl Chloride

Product 1

HCID 75736Methyl L-phenylalaninate hydrochlorideYield 100%

Procedure

To a stirred solution of L-phenylalanine (6) (40 g, 242 mmol) in methanol (193 ml) at -10° C. was added thionyl chloride (19.45 ml, 266 mmol) and the solution was refluxed for 2 hours. After concentration in vacuo the compound was recrystallised from methanol-diethyl ether mixture giving the title ester (7) (52.23 g, 100%); δH (D2O; 200 MHz) 2.95-3.18 (2H, m, CH2CH), 3.62 (3H, s, CH3), 4.21 (1H, dd, J=6.1 and 7.4, CH2CH), 4.59 (2H, s, NH2), 7.06-7.27 (5H, m, ArCH).

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. concentrationAfter concentration in vacuo the compound
  3. customwas recrystallised from methanol-diethyl ether mixture

Sources & evidence

ORD record
ord-151df93236ea48608e4e86354a5de6aa
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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