Reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C@@H:11]1[CH2:16][N:15]([C:17]([O:19][CH3:20])=[O:18])[C@H:14]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)=[O:22])[C@@H:13]([C:35](OC)=[O:36])[CH2:12]1)=[O:9].[OH:39][NH2:40].Cl.NO.C[O-].[Na+].Cl>CO>[OH:39][NH:40][C:35]([C@H:13]1[CH2:12][C@H:11]([O:10][C:8]([N:4]2[CH2:5][CH2:6][CH2:7][C@H:3]2[CH2:2][OH:1])=[O:9])[CH2:16][N:15]([C:17]([O:19][CH3:20])=[O:18])[C@@H:14]1[C:21]([N:23]1[CH2:24][CH2:25][N:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:27][CH2:28]1)=[O:22])=[O:36]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of dimethyl (2S,3S,5S)-5-([(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyloxy)-2-[(4-phenylpiperazin 1-yl)carbonyl]piperidine-1,3-dicarboxylate (66 mg, 0.00012 mol) in methanol (0.57 mL, 0.014 mol) was added 1.640 M of N-hydroxyamine in methanol solution (1.511 mL), made from the hydroxylamine HCl salt and sodium methoxide freshly. The mixture was stirred at rt for 1 h and acidified with 1N HCl. The resulting mixture was applied directly on RP-HPLC to yield the desired compound (61 mg, 76%). MS (ESI): (M+H)+=534.2.
Sources & evidence
- ORD record
- ord-6bc0f5e28c7f44e695714fca425d03c7
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853243B2
Linked notes
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