反応 #1885041

反応方程式

(S)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide

4-methoxybenzenesulfonyl chloride

DIEA

→

(S)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(4-methoxyphenylsulfonyl)-N-(thiazol-2-yl)benzenesulfonamide

収率 89.2%

溶媒

MeOH

water

DMF

反応条件

後処理

1. 1
   その他Synthesized
2. 2
   その他the resulting precipitated solid
3. 3
   ろ過was collected by vacuum filtration
4. 4
   洗浄The precipitate was washed with water

実験手順

Synthesized according to General Procedure 8. A solution of (S)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (150 mg, 0.44 mmol), 4-methoxybenzenesulfonyl chloride (91 mg, 0.44 mmol) and DIEA (57 mg, 77 μL, 0.44 mmol) in DMF (0.75 mL) was stirred at room temperature for 1 h. The reaction mixture was diluted with MeOH (1 mL) and water (10 mL), and the resulting precipitated solid was collected by vacuum filtration. The precipitate was washed with water followed by cold Et2O to afford the product, (S)-4-(3-hydroxy-2-oxopyrrolidin-1-yl)-N-(4-methoxyphenylsulfonyl)-N-(thiazol-2-yl)benzenesulfonamide (200 mg, 0.3925 mmol) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 7.86-7.80 (m, 4H), 7.70 (d, J=5.1 Hz, 1H), 7.60 (d, J=9.0 Hz, 2H), 7.03-6.98 (m, 3H), 5.88 (d, J=5.9 Hz, 1H), 4.38-4.32 (m, 1H), 3.85-3.77 (m, 1H), 3.81 (s, 3H), 3.70 (td, J=9.4, 5.4 Hz, 1H), 2.48-2.41 (m, 1H) and 1.92-1.82 (m, 1H) ppm. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=510.0; tR=1.22 min.

出典