Methanol → (S)-Methyl 2-amino-3-(4-methoxyphenyl)propanoate hydrochloride

HRID 2399918Notes

Reaction equation

HRID 2399918 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])=[CH:5][CH:4]=1.S(Cl)([Cl:17])=O.[CH3:19]O>>[ClH:17].[CH3:19][O:11][C:10](=[O:12])[C@H:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][CH:13]=1)[NH2:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2723935O-Methyl-L-Tyrosine

Product 1

HCID 69612215(S)-Methyl 2-amino-3-(4-methoxyphenyl)propanoate hydrochloride

Procedure

A solution of O-methyl-L-tyrosine (1.44 g, 7.4 mmol) in methanol (30 ml) was stirred at 0° C. and thionyl chloride (1 ml, 13.4 mmol) added dropwise. After stirring for 15 min. at ambient temperature the reaction was heated at reflux for 2 h. After cooling the solvent was evaporated to give crude O-methyl-L-tyrosine methyl ester hydrochloride salt as a yellow solid. This was partitioned between saturated aqueous sodium hydrogen carbonate (80 ml) and ethyl acetate (150 ml), and the aqueous layer back extracted with ethyl acetate (2×80 ml). The combined organics were dried over anhydrous s odium sulphate, filtered and concentrated to give O-methyl-L-tyrosine methyl ester as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling the solvent
  4. customwas evaporated

Sources & evidence

ORD record
ord-06fa6b7161b74ace9b4e9094cfa65608
Source dataset
uspto-grants-1995_09
Patent number
US05451676

Reaction notes

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