反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
PROCEDURE
实验过程
To a solution of (2S)-2-(tert-butoxy)-2-[(20S)-16-chloro-4,20,26-trimethyl-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, 0.032 mmol) in ethanol (1 mL) was added Hoveyda-Grubbs catalyst 2nd generation (4.00 mg, 6.38 μmol). Sodium borohydride (6.03 mg, 0.159 mmol) was added and the mixture was stirred at rt. After 30 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)-16-chloro-4,20,26-trimethyl-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 (6.1 mg, 9.70 μmol, 30.4% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.32 (d, J=8.1 Hz, 1H), 7.06 (s, 1H), 6.94 (d, J=8.1 Hz, 1H), 6.48 (s, 1H), 5.63 (br. S., 1H), 4.84 (d, J=12.5 Hz, 1H), 4.69-4.48 (m, 4H), 4.32 (t, J=11.9 Hz, 1H), 3.65 (br. S., 1H), 3.35-3.22 (m, 4H), 2.74 (s, 3H), 2.02-1.40 (m, 10H), 1.26-0.95 (m, 15H). LCMS (M+H) calcd for C33H46ClN4O6: 629.31. found: 629.4.
WORKUP
后处理
- customthe reaction was quenched by careful addition of water
- extractionThe product was extracted with EtOAc
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified via preparative HPLC