Water → HCID 23123890, compound

HRID 511753Notes

Reaction equation

HRID 511753 reaction equation
[H-].[Na+].[Cl:3][C:4]([Cl:22])([Cl:21])[CH2:5][O:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:8].S(OC)(O[CH3:27])(=O)=O.O>O1CCCC1>[CH3:27][N:9]([C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]([O:6][CH2:5][C:4]([Cl:21])([Cl:22])[Cl:3])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 23123796HCID 23123796, compound

Product 1

HCID 23123890HCID 23123890, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 0.14 g of 60% sodium hydride in 5 ml of tetrahydrofuran was dropwise added a solution of 1.0 g of ethyl 3-(2,2,2-trichloroethoxycarbonylamino)benzoate in 5 ml of tetrahydrofuran, and the resultant mixture was stirred at room temperature. Then, a solution of 0.45 g of dimethyl sulfate in 5 ml of tetrahydrofuran was dropwise added, and the resultant mixture was stirred at room temperature for 3 hours. After water was added to the mixture, the mixture was subjected to extraction with ethyl acetate, and an organic layer was washed twice with water and dried with anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane ethyl acetate=4:1) to obtain 0.84 g (yield 79%) of the title compound as an oily material.

Workup

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. washan organic layer was washed twice with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; hexane ethyl acetate=4:1)

Sources & evidence

ORD record
ord-493f0fe343134252b3e738114e118900
Source dataset
uspto-grants-2015_08
Patent number
US09101135B2

Reaction notes

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