Diethyl Carbonate → HCID 14722309, compound

HRID 1031679Notes

Reaction equation

HRID 1031679 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

4

Reactant 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 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.

Workup

  1. washThe resulting mixture was washed with 50 ml of diethyl ether
  2. customThe aqueous layer was separated
  3. extractionextracted with two 100-ml portions of ethyl acetate
  4. washwashed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by a column chromatography (eluant
  8. additiona 3 : 1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-8f55a93b66c349fe8004e644fe30a817
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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