反応 #6480

反応方程式

acetic anhydride

N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-hydroxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide

→

title compound

N-[4-[5-(Cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-acetoxy- 3-methyl-but-1-yn-1-yl)-benzenesulfonamide

溶媒

pyridine

ethyl acetate

反応条件

後処理

1. 1
   洗浄The ethyl acetate phase is washed twice with 80 ml of 1N hydrochloric acid each time
2. 2
   乾燥The ethyl acetate phase is dried over magnesium sulfate
3. 3
   濃縮concentrated by evaporation at 20 torr and 40°
4. 4
   その他The residue is chromatographed on 50 g of silica gel (Merck, ST 60, 40-63 μm) with hexane/ethyl acetate=1/1

実験手順

0.44 g of acetic anhydride and 0.1 g of 4-dimethylaminopyridine are added to a solution of 1.0 g of N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-hydroxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide in 6 ml of pyridine. The reaction solution is stirred for 20 hours at room temperature under argon. The reaction mixture is subsequently diluted with 100 ml of ethyl acetate. The ethyl acetate phase is washed twice with 80 ml of 1N hydrochloric acid each time, with 50 ml of water and with 50 ml of saturated sodium chloride solution. The ethyl acetate phase is dried over magnesium sulfate and concentrated by evaporation at 20 torr and 40°. The residue is chromatographed on 50 g of silica gel (Merck, ST 60, 40-63 μm) with hexane/ethyl acetate=1/1 to yield the title compound in the form of a white amorphous solid. 1H-NMR (400 MHz, DMSO-d6): 8.87 (b, 1H); 8.06 (d, d, 1H); 7.61 (m, 3H); 7.55 (d, 1H); 7.50 (d, 1H); 7.41 (d, d, 1H); 7.22 (d, 1H); 7.14 (d, d, 1H); 7.13 (d, 1H); 6.94 (s, 1H); 5.06 (m, 1H); 3.95 (s, 2H); 3.90 (s, 3H); 3.66 (s, 3H); 1.91 (s, 3H); 1.89-1.52 (m, 8H); 1.61 (s, 6H).

出典