Methanol → HCID 15617483, compound

Participants

Reaction Steps

The compound of Example 3(a) (1.2 g, 3.28 mmoles) was dissolved in methanol (20 ml) containing 2% triethylamine and stirred under argon at room temperature. Methyl 3-mercaptopropionate (0.623 ml, 5.45 mmoles) and triethylamine (1.45 ml, 9.84 mmoles) were dissolved in methanol (15 ml) and added dropwise. The mixture was stirred for 18 hours. The solvent was stripped and the residue was flash chromatographed on silica gel eluted with 20% ethyl acetate/hexane to give a mixture of the desired product and its regioisomer, methyl 2-(2-carbomethoxyethylthio)-3-[2-(8 phenyloctyl)phenyl]-3-hydroxypropanoate. The mixture was rechromatographed on 100 grams of neutral alumina to separate the desired product.

Provenance & Evidence