Acetyl chloride → HCID 89620183, compound

Reaction equation

Cl.Cl.Cl.[NH2:4][C:5]1[C:10]2=[C:11]([C:29]3[S:30][C:31]4[C:37]([O:38][CH3:39])=[CH:36][C:35]([CH3:40])=[CH:34][C:32]=4[CH:33]=3)[C:12]([CH2:21][N:22]3[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH2:23]3)=[C:13]([CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[N:9]2[N:8]=[CH:7][N:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:47](Cl)(=[O:49])[CH3:48]>ClCCl.C1COCC1>[C:47]([N:18]1[CH2:17][CH2:16][N:15]([CH2:14][C:13]2[N:9]3[C:10]([C:5]([NH2:4])=[N:6][CH:7]=[N:8]3)=[C:11]([C:29]3[S:30][C:31]4[C:37]([O:38][CH3:39])=[CH:36][C:35]([CH3:40])=[CH:34][C:32]=4[CH:33]=3)[C:12]=2[CH2:21][N:22]2[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH2:23]2)[CH2:20][CH2:19]1)(=[O:49])[CH3:48]

Participants

Procedure

A suspension of Example 49 (310 mg, 522 μmol) in dichloromethane/THF (2.5:1, 9.64 ml) was treated with sodium carbonate (442 mg, 4.17 mmol) and stirred at rt for 30 min. Acetyl chloride (74 μl, 1.04 mmol) was added, and the resulting mixture was stirred at rt for 2 h. After quenching with methanol, the mixture was evaporated, and the residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid) affording 133 mg (45% of th.) of the title compound.