Acetic Anhydride → HCID 66818857, compound

Reaction equation

C(OC(=O)C)(=O)C.[C:8]([O:12][C:13](=[O:54])[NH:14][CH:15]1[CH2:20][CH2:19][CH:18]([C:21](=[O:53])[NH:22][C:23]2[CH:28]=[C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([C:37](=[NH:40])[NH:38]O)=[CH:33][CH:32]=3)[CH:26]=[C:25]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][C:46]([C:49](=[NH:52])[NH:50]O)=[CH:45][CH:44]=3)[CH:24]=2)[CH2:17][CH2:16]1)([CH3:11])([CH3:10])[CH3:9]>C(O)(=O)C.[Zn]>[C:8]([O:12][C:13](=[O:54])[NH:14][CH:15]1[CH2:20][CH2:19][CH:18]([C:21](=[O:53])[NH:22][C:23]2[CH:24]=[C:25]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][C:46]([C:49](=[NH:50])[NH2:52])=[CH:45][CH:44]=3)[CH:26]=[C:27]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([C:37](=[NH:38])[NH2:40])=[CH:35][CH:36]=3)[CH:28]=2)[CH2:17][CH2:16]1)([CH3:11])([CH3:9])[CH3:10]

Participants

Procedure

Acetic anhydride (0.36 ml, 3.72 mmol) was added to the solution of (4-{3,5-bis-[4-(N-hydroxycarbamimidoyl)-benzyloxy]-phenylcarbamoyl}-cyclohexyl)-carbamic acid tert-butyl ester (0.40 g, 0.62 mmol) in 10 ml of acetic acid and reaction mixture was stirred for 3 h. After completion of reaction, at RT zinc dust (0.4 g, 6.2 mmol) was added and resulting mixture was stirred over night. Recation mixture was filtered through celite and filterate was concentrated to dryness. Product was washed with cold diethyl ether and dried to afford 0.52 g of the required product. Percentage purity (LCMS): 100.0%, (M−1)=615.2-1.