Triethylamine → Methyl Nalpha-[3-(2-Acetoxyphenyl)acryloyl]-L-Tryptophanate

Participants

Reaction Steps

Triethylamine (4.8 mL), 2-acetoxycinnamic acid (7.1 g) and WSC.HCl (6.6 g) were added to a methylene chloride (180 mL) suspension of methyl L-tryptophanate hydrochloride (7.3 g) at 0° C. The mixture was stirred for 20 hours at room temperature. The reaction mixture was washed with water, and thereafter the organic layer was dried over anhydrous sodium sulfate. The residual oily product obtained by distilling off the solvent under a reduced pressure was purified by silica gel column chromatography (BW-127ZH, chloroform:methanol=100:1), to give the captioned compound (8.9 g, 76%) as crystals.

Provenance & Evidence