Methanol → HCID 18315358, compound

HRID 275876Notes

Reaction equation

[OH-].[Na+].CO.C[O:6][C:7](=[O:37])[CH2:8][CH:9]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:17]=2)[C:13]2[CH:31]=[C:32]([Cl:35])[CH:33]=[CH:34][C:12]=2[NH:11][C:10]1=[O:36]>O>[C:27]([O:26][C:24]([NH:23][CH2:22][C:18]1[CH:17]=[C:16]([C:14]2[C:13]3[CH:31]=[C:32]([Cl:35])[CH:33]=[CH:34][C:12]=3[NH:11][C:10](=[O:36])[CH:9]([CH2:8][C:7]([OH:37])=[O:6])[N:15]=2)[CH:21]=[CH:20][CH:19]=1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

Conditions

Temperature: 60 °C

Procedure

A 1N aqueous solution of sodium hydroxide (1.5 ml) was added to a methanol solution (6 m.) of 5-(3-tert-butyloxycarbonylaminomethylphenyl)-7-chloro-2,3-dihydro-2-oxo-1H-1,4-benzodiazepine-3-acetic acid methyl ester (0.6 g), the compound produced in Example 97-(1). The mixture was stirred for 2 hours at 60° C. The reaction mixture was diluted with water (50 ml), which was acidified, followed by extraction with ethyl acetate (50 ml) twice. The extracts were combined and washed with a saturated aqueous saline solution, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 5-(3-tert-butyloxycarbonylaminomethylphenyl)-7-chloro-2,3-dihydro-2-oxo-1H-1,4-benzodiazepine-3-acetic acid (0.64 g) as a colorless amorphous solid product.

Workup

extractionfollowed by extraction with ethyl acetate (50 ml) twice
washwashed with a saturated aqueous saline solution
dry with materialby drying over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-2e1561014b434e7b8fe0ad2716f4f798
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352982B1

Reaction notes

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