Methanol → (+/-)-1-Acetyl-7-[[(6-amino-2-pyridinyl)amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetic acid
Reaction equation
[OH-].[Na+].[C:3]([N:6]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[N:21]=3)=[O:18])=[CH:16][C:11]=2[CH2:10][N:9]([CH3:27])[C:8](=[O:28])[CH:7]1[CH2:29][C:30]([O:32]C)=[O:31])(=[O:5])[CH3:4].CO>O>[C:3]([N:6]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[N:21]=3)=[O:18])=[CH:16][C:11]=2[CH2:10][N:9]([CH3:27])[C:8](=[O:28])[CH:7]1[CH2:29][C:30]([OH:32])=[O:31])(=[O:5])[CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1 N NaOH (1.0 mL, 1.0 mmol) was added to a cold solution of methyl (±)-1-acetyl-7-[[(6-amino-2-pyridinyl)amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (0.23 g, 0.54 mmol), MeOH (2 mL) and H2O (1 mL). The solution was stirred at room temperature for 18 h then was concentrated. Chromatography (ODS, 10% CH3CN/H2O-0.1% TFA) gave the title compound (0.215 g, 90%): 1H NMR (400 MHz, DMSO-d6) δ1.7-1.9 (s, 3H), 2.0-2.6 (m, 2H), 3.0-3.1 (s, 3H), 4.1-4.2 (d, 1H), 4.7-4.8 (d, 1H), 5.7-5.9 (m, 1H), 6.4-6.5 (d, 1H), 7.0-7.1 (d, 1H), 7.5-7.6 (d, 1H), 7.6-7.8 (t, 1H), 8.0-8.1 (d, 1H), 8.2-8.3 (s, 1H); MS (ES) m/e 412.2 (M+H)+. Anal. Calcd for C20H21N5O5.2.75 CF3CO2H: C, 42.25; H, 3.30; N, 9.66. Found: C, 42.01; H, 3.25; N, 9.85.
Workup
- concentrationthen was concentrated
Sources & evidence
- ORD record
- ord-2f1edb86050b413aa07e3bbc54da7a3b
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06458784B1
Reaction notes
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