1-Hydroxybenzotriazole → Carbamate

Participants

Reaction Conditions

Reaction Steps

Dissolve the product of Step 2 (134 g) in CH2Cl2 (1.5 L). Treat sequentially with HOBT (44.6 g), BOC-D-phenylglycine (86.3 g) and DEC (65.9 g). Stir the mixture at 23° C. for 18 h, heat at reflux temperature for 2 h, recool to 23° C., treat with saturated NaHCO3 solution (500 mL), separate the organic portion, dry (MgSO4), filter and concentrate. Recrystallize the crude material, once from Et2O and twice from iPr2O to give 1,1-dimethylethyl-[[[1-[[(3,5-dichlorobenzoyl)methylamine]methyl]-2-(3,4-dichlorophenyl)-5-methyl-hexen-1-ylidene]amino]oxy]-2-oxo-1-phenylethyl]carbamate (51 g). MS(FAB): m/e 722; [α]D 23 =-96.9° (c 0.4 CH2Cl2); m.p. 98-102° C. (dec).

Provenance & Evidence