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 compound 132 (18 mg, 0.689 mmol) in pyridine (2.8 mL) was added 4-acetamidobenzoyl chloride (150 mg, 0.758 mmol) and 4-(dimethylamino)pyridine (8 mg, 0.07 mmol) and the mixture was stirred for 16 h. at r.t. Then, it was partitioned between EtOAc and H2O, The aqueous layer was extracted with fresh EtOAc and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting crude oil was purified by flash chromatography on silica gel using methanol/EtOAc (5:95) as the eluent affording the title compound 133 (47 mg, 16% yield) as a 1:1 mixture with 4-acetamidobenzoic acid (hydrolyzed starting material). 1H NMR: (Acetone-d6) δ(ppm): 10.76 (bs, 1H), 9.52 (bs, 1H), 9.00 (d, J=1.0 Hz, 1H), 8.20 (d, J=7.2 Hz, 1H), 7.99 (d, J=8.6 Hz, 2H), 7.85 (d, J=8.6 Hz, 2H), 7.64 (dd, J=8.2, 1.2 Hz, 1H), 2.15 (s, 3H), 1.40 (s, 12H).
WORKUP
后处理
- customThen, it was partitioned between EtOAc and H2O
- extractionThe aqueous layer was extracted with fresh EtOAc
- washthe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting crude oil was purified by flash chromatography on silica gel