Hydrogen Bromide → (13E)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[1-(3-phenyloxiran-2-yl)ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone

Participants

Reaction Steps

A solution of 7 mg of Cryptophycin 38 in 1 mL of dimethoxyethane was treated with 10 μL of 30% HBr in acetic acid at 50° C. for 18 hours. The mixture was brought to the ambient temperature and stirred with 20 mg of powdered dry potassium carbonate for 3 hours. The solution was filtered, the solvent evaporated and the residue subjected to HPLC on an Econosil silica column (250×10 mm, 5μ, 1:1 ethylacetate/hexane, 3 mL/min) to obtain 3.3 mg of crypptophycin 71 (tR 49.6 min) and 2.8 mg of cryptophycin 72 (tR 46 min).

Provenance & Evidence