4-Methylmorpholine → HCID 178455656, compound

Reaction equation

[CH2:1]([S:5]([NH:8][C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[C:15]([C:17]1[CH:29]=[CH:28][C:20]([CH2:21][NH:22][C:23](=[O:27])[C@H:24]([CH3:26])[NH2:25])=[CH:19][CH:18]=1)#[N:16].Cl.[NH2:31][OH:32].CN1CCOCC1>CO>[CH2:1]([S:5]([NH:8][C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4].[OH:32][NH:31][C:15]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][NH:22][C:23](=[O:27])[C@H:24]([CH3:26])[NH2:25])=[CH:28][CH:29]=1)=[NH:16]

Participants

Procedure

To a solution of the product in Example 7 (117 mg, 0.285 mmol) in 1.14 ml methanol was added hydroxylamine hydrochloride (33.7 mg, 0.485 mmol), followed by N-methylmorpholine (53 μl, 0.485 mmol). The reaction mixture was stirred overnight at ambient temperature and then at 50° C. for six hours. The reaction mixture was concentrated in vacuo. The crude product was taken to the next step (Example 9) without further purification. The product eluted at 6.5 minutes by reverse phase (C18) HPLC at 0.1% trifluoroacetic acid in 5-50% aqueous acetonitrile over 20 minutes.