Diethyl Carbonate → HCID 14722309, compound

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:12]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:11][C:10]=1[C:27]([CH3:29])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](=O)([O:34]CC)[O:31][CH2:32][CH3:33].[H-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:12]([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:11][C:10]=1[C:27]([CH2:29][C:30]([O:31][CH2:32][CH3:33])=[O:34])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7766Diethyl Carbonate

HCID 24758Sodium hydride

HCID 10549566HCID 10549566, compound

Product 1

HCID 14722309HCID 14722309, compoundYield 90%

Procedure

There were mixed 4.11 g of methyl 2-benzyloxy-4-methylsulfonylamino-5-phenoxyphenyl ketone, 20.6 ml of diethyl carbonate, 20.6 ml of N,N-dimethylformide and 1.6 g of sodium hydride (purity: 60%). The mixture was stirred for 30 minutes at 90°-100° C. The reaction mixture was introduced into 200 ml of ice water. The resulting mixture was washed with 50 ml of diethyl ether. The aqueous layer was separated, adjusted to pH 5 with 4N hydrochloric acid, and extracted with two 100-ml portions of ethyl acetate. The extracts were combined, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: a 3 : 1 mixture of toluene and ethyl acetate) to obtain 4.35 g (yield: 90%) of ethyl 2-(2-benzyloxy-4-methylsulfonylamino-5-phenoxybenzoyl)acetate.