1,2-Dichloroethane → benzyl 4-{[({(7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-11-yl}carbonyl)amino]sulfonyl}butanoate

Participants

Reaction Steps

Benzyl 4-(aminosulfonyl)butanoate (1.3 eq)(prepared as described in step 1), DMAP (2.5 eq) and EDC (1.5 eq), were added to a solution of (7R)-7-[{2-[(tert -butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid (0.03 M) in DCM. The reaction was stirred under N2 at RT for 24h, before volatiles were removed in vacuo to leave the crude product as a yellow gum, which was purified by automated RP-HPLC (WATERS XTERRA column; MeCN/H2O/0.1% TFA gradient). Fractions containing the pure compound were combined and lyophilized to afford the product as a white powder (37%). (ES+) m/z 787 (M+H)+

Provenance & Evidence