Piperidine → HCID 86718404, compound

Participants

Reaction Steps

Synthesis of (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-7-(2- amino-2-oxoethyl)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl piperidine-1-carboxylate (#B135). Using the procedure described in step 3 of example A42, the title compound was prepared in 18% yield from 63.2 mg (0.104 mmol, 1.0 eq) of #B132, triethylamine (73 μL, 0.520 mmol, 5 eq), 4-N,N-dimethylamino pyridine (8.9 mg, 0.073 mmol, 0.7 eq.) and bis-(4-nitrophenyl)-carbonate (106 mg, 0.343 mmol, 3.3 eq.) and piperidine (14.8 mg, 0.174 mmol, 1.7 eq.) using the procedure described for preparation of compound #B133. LCMS (Protocol D): m/z 740.5 [M+Na]+, retention time=1.13 minutes.

Provenance & Evidence