tert-Butanol → HCID 86701265, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-((3S,7R,8R,9S)-3-(tert-butoxycarbonylamino)-8-(isobutyryloxy)-9-methyl-2,6-dioxo-1,5-dioxonan-7-yl)acetic acid (400 mg, 0.928 mmol) in CH2Cl2 (2 mL) was added tert-butyl alcohol (3.44 mg, 4.64 mmol) and DMAP (91 mg, 0.744 mmol) at room temperature (about 22° C.). The solution was cooled to 0° C. and N,N′-methanediylidenedipropan-2-amine (172 uL, 1.11 mmol) was added. The reaction mixture was warmed to room temperature, stirred for 2 h, and then loaded directly onto a SiO2 column and purified by flash chromatography (hexanes/EtOAc gradient) to give the title compound (380 mg, 84%) as a white solid: mp 170-172° C.; 1H NMR (400 MHz, CDCl3) δ 5.44-5.15 (m, 2H), 5.08-4.94 (m, 1H), 4.93-4.75 (m, 2H), 3.74-3.54 (m, 1H), 2.98-2.87 (m, 1H), 2.83-2.71 (m, 1H), 2.61 (hept, J=7.0 Hz, 1H), 2.32-2.21 (m, 1H), 1.44 (s, 9H), 1.40 (s, 9H), 1.27 (d, J=6.3 Hz, 3H), 1.21 (dd, J=7.0, 1.6 Hz, 6H); ESIMS m/z 410 ([M+Na]+).

Provenance & Evidence