Sodium Iodide → HCID 18001014, compound

HRID 1249996Notes

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-61d2d09264744744b6eacd1ffae1c366
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06335327B1

Reaction notes

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