Triethylamine → HCID 86746114, compound

Participants

Reaction Steps

A solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-triisopropylsilyloxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (150 mg, 0.16 mmol) in MeCl2 (5.0 ml) containing triethylamine (92.2 mg, 0.91 mmol) and 4-dimethylaminopyridine (61 mg, 0.49 mmol) at 0° C., was treated with methanesulfonyl chloride (69.6 mg, 0.61 mmol). After stirring at RT for 2.5 hr, the reaction mixture was diluted with MeCl2 (10 ml) and water. The aqueous layer was separated and extracted with additional MeCl2. After drying over magnesium sulfate, the solvent was removed in vacuo. The residue was chromatographed over SiO2 (10 g). Elution with n-hexane/ethyl acetate (3:1) yielded 17-ethyl-1-hydroxy-12-[2'-(4"-triisopropylsilyloxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos- 14,18-diene-2,3,10,16-tetraone (86.6 mg, 58%). Mass Spec: C52H89NO11Si (930.36) FAB+Li:1090 (M+ +Li+MATRIX) 936 (M+Li).

Provenance & Evidence