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L-4-CHLOROPHENYLALANINE METHYL ESTER HCL synthesis

7synthesis methods
176896-73-4 Synthesis
(S)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID METHYL ESTER

176896-73-4
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Yield:63024-26-0 93%

Reaction Conditions:

with hydrogenchloride in ethyl acetate; for 2.5 h;

Steps:

31.B

Step B: (2S)-2-tert-Butoxycarbonylamino-3-(2-naphthyl)propionic acid methyl ester (5.52 g, theoretically 15.85 mmol) is dissolved in 20 ml of ethyl acetate in a 500 ml flask equipped with a magnetic stirrer. To the stirred solution is added 80 ml of 2.8 M hydrogen chloride in ethyl acetate and the reaction is stirred for 2.5 hours under nitrogen. The clear mixture is concentrated in vacuo to give a solid, which is taken up in ethyl acetate, stirred for 10 min and filtered. The solid is dried in vacuo at 40° C. to give 3.91 g (93%) of (2S)-2-Amino-3-(2-naphthyl)propionic acid methyl ester hydrochloride as a white solid. HPLC-MS: Rt=3.70 min., (M+1)=230, % Area by ELS=100

References:

US2007/185128,2007,A1 Location in patent:Page/Page column 27