反应详情

To a solution of (2S)-2-(tert-butoxy)-2-[(20S)-4,15,20,26-tetramethyl-11,19,25-trioxa-1,5,7,8-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13,15,17,22-octaen-3-yl]acetic acid (0.020 g, 0.033 mmol) in ethanol (1 mL) was added Hoveyda-Grubbs catalyst 2nd generation (4.13 mg, 6.59 μmol). Sodium borohydride (6.24 mg, 0.165 mmol) was added and the mixture was stirred at rt. After 45 min, the reaction was quenched by careful addition of water. The product was extracted with EtOAc, dried (Na2SO4), filtered and concentrated. The crude material was purified via preparative HPLC to afford (2S)-2-(tert-butoxy)-2-[(20S)-4,15,20,26-tetramethyl-11,19,25-trioxa-1,5,7,8-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13,15,17-heptaen-3-yl]acetic acid (2.1 mg, 9.94% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.14 (s, 1H), 7.04-6.95 (m, 1H), 6.86 (d, J=8.4 Hz, 1H), 6.42 (s, 1H), 4.83 (d, J=12.5 Hz, 1H), 4.62-4.42 (m, 3H), 4.39-4.26 (m, 1H), 3.47-3.31 (m, 3H), 2.85-2.74 (m, 1H), 2.64 (br. s., 1H), 2.42-2.33 (m, 1H), 2.23 (s, 3H), 2.02-1.30 (m, 14H), 1.28-0.96 (m, 15H). LCMS (M+H) calcd for C34H49N4O6: 609.36. found: 609.4.

1. customthe reaction was quenched by careful addition of water
2. extractionThe product was extracted with EtOAc
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude material was purified via preparative HPLC