Hydrochloric Acid → HCID 12017660, compound

HRID 1006531Notes

Reaction equation

HRID 1006531 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:7]=1[O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)=O.C1COCC1.CO.C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[NH2:5][C:6]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:7]=1[O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 12017659HCID 12017659, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 12017660HCID 12017660, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-(2-trifluoroacetylamino-5-chlorophenoxy-methyl)benzoate (300 mg; prepared in Reference Example 6.) in mixture of THF-MeOH (4 ml+10 ml), a solution of sodium carbonate (440 mg) in water (2 ml) was added. The solution was stirred for 8 hours at 60° C. and overnight at room temperature. The reaction mixture was poured into diluted HCl and extracted with ethyl acetate. The organic layer was washed, dried over and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (AcOEt-benzene) to give the title compound (194 mg) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried over and
  4. concentrationconcentrated under the reduced pressure
  5. customThe residue was purified on silica gel column chromatography (AcOEt-benzene)

Sources & evidence

ORD record
ord-2e9d6c96815e4aab8661b7e2d1671961
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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