ChemicalBook CAS DataBase List (S)-3,4-DIMETHOXYPHENYLALANINE METHYL ESTER

(S)-3,4-DIMETHOXYPHENYLALANINE METHYL ESTER synthesis

7synthesis methods

Product Name:(S)-3,4-DIMETHOXYPHENYLALANINE METHYL ESTER
CAS Number:78083-80-4
Molecular formula:C12H17NO4
Molecular Weight:239.27

67-56-1 Synthesis

67-56-1
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32161-30-1
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(S)-3,4-DIMETHOXYPHENYLALANINE METHYL ESTER

78083-80-4
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Yield:78083-80-4 100%

Reaction Conditions:

with thionyl chloride at 0; for 10 h;Reflux;

Steps:

25 (S)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-amine

Example 25
(S)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-amine
3,4-dimethoxy-L-phenylalanine (100.0 g, 0.44 mol) was added to 1.3 L of methanol and the solution was cooled to 0° C. with an ice-water bath.
Thionyl chloride (48 mL, 0.66 mol) was added slowly to the chilled solution.
The ice bath was removed and the reaction mixture was heated at reflux for 10 hours.
The solution was allowed to cool to room temperature and the methanol was removed by rotary evaporation.
The oily residue was dissolved in 250 mL of deionized water, and the resulting solution was brought to pH 12 with saturated aqueous sodium carbonate.
The aqueous solution was extracted with dichloromethane (5*300 mL) and the combined organic extracts were dried with sodium sulfate, filtered, and evaporated to yield (S)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-amine (106 g, quant.) as a light yellow oil.

References:

US2014/121371,2014,A1 Location in patent:Paragraph 0411

138908-56-2 Synthesis