Sodium Iodide → HCID 18001014, compound

HRID 1870462Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](=[O:33])[C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]([O:28][CH2:29][CH2:30]Cl)=[O:27])=[CH:21][C:20]=2[Cl:32])[CH2:10][CH2:9][CH2:8]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](=[O:33])[C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][O:28][C:26]3=[O:27])=[CH:21][C:20]=2[Cl:32])[CH2:10][CH2:9][CH2:8]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-ethoxycarbonylmethyl-1-[4-(2-chloroethoxycarbonylamino)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (0.9 g), potassium carbonate (0.40 g) and sodium iodide (0.43 g) in dimethylformamide (15 ml) is stirred at 80° C. for 8 hours. To the reaction solution is added ethyl acetate, and the mixture is washed with water, and the organic layer is dried over magnesium sulfate, filtered, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=30:1) to give 5-ethoxycarbonylmethyl-1-[4-(2-oxotetrahydrooxazol-3-yl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (0.65 g) as colorless amorphous.

Workup

washthe mixture is washed with water
dry with materialthe organic layer is dried over magnesium sulfate
filtrationfiltered
customevaporated
customto remove the solvent
customThe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=30:1)

Sources & evidence

ORD record: ord-bd1d6024f77e4c59b7843b0539ead2d7
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06096735

Reaction notes

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