Acetyl chloride → HCID 10178010, compound

Reaction equation

[H-].[K+].[C:3]1([CH:13]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][N:17]3[C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[S:14]2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[C:28](Cl)(=[O:30])[CH3:29]>C1COCC1>[C:28]([O:20][C:19]1[C:18]2=[CH:21][CH:22]=[CH:23][N:17]2[C:16]2[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=2[S:14][C:13]=1[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)(=[O:30])[CH3:29]

Participants

Procedure

To a suspension of potassium hydride (0.303 g, 2.64 mmol, 35% in oil) in anhydrous THF (5.0 mL) was added the (±)-6-(1-naphthyl)pyrrolo[2,1-d][1,5]benzothiazepin-7(6H)-one (0.9 g, 2.64 mmol) dissolved in anhydrous THF (7 mL). The reaction mixture was stirred at rt for 2 h, and then acetyl chloride (0.239 g, 3.04 mmol) was slowly added. After stirring for 12 h at rt, the solvent was removed in vacuo and the residue was dissolved in chloroform. The organic layer was washed with brine, dried and concentrated. The residue was chromatographed (dichloromethane and hexane 1:1) to give the PBOX-9 in 86% yield. IR (neat) 1762 cm−1; 1HNMR (CDCl3) δ 1.70 (s, 3 H) 6.45 (m, 1 H), 6.63 (m, 1 H), 7.19-7.55 (m, 10 H), 7.78-7.87 (m, 2 H).