Water → HCID 53945920, compound

HRID 1708576Notes

Reaction equation

HRID 1708576 reaction equation
C(Cl)Cl.[CH3:4][S:5][C:6]1[CH:7]=[C:8]([CH2:20][C:21]([OH:23])=[O:22])[CH:9]=[C:10]2[C:15]=1[NH:14][CH:13]([C:16]([F:19])([F:18])[F:17])[CH2:12][CH2:11]2.Cl[C:25]1C=CC=C(C(OO)=O)C=1.C(=O)([O-])O.[Na+].[OH2:40]>>[CH3:4][S:5]([C:6]1[CH:7]=[C:8]([CH2:20][C:21]([O:23][CH3:25])=[O:22])[CH:9]=[C:10]2[C:15]=1[NH:14][CH:13]([C:16]([F:17])([F:18])[F:19])[CH2:12][CH2:11]2)=[O:40]

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 18959582HCID 18959582, compound

Product 1

HCID 53945920HCID 53945920, compound

Procedure

Into 30 ml of methylene chloride were dissolved 1.17 g of methyl ester of 8-methylthio-1,2,3,4-tetrahydro-2-trifluoromethylquinoline-6-acetic acid, and the mixture was stirred under cooling with ice. To this were added 870 mg of m-chloroperbenzoic acid and 336 mg of sodium hydrogen-carbonate, and the mixture was stirred for 1 hours. Water was added and the reaction mixture was extracted with methylene chloride, which was washed with saturated aqueous sodium bicarbonate, with water and with saturated saline solution and then dried over anhydrous sodium sulfate. Solvent was distilled off and the residue was purified by means of silica gel chromatography (development solvent; ethyl acetate:hexane=1:1) to obtain 620m g of dia-stereoisomer A and 300 mg of diastereoisomer B of methyl 8-methylsulfinyl-1,2,3,4-tetrahydro-2-trifluoromethylquinoline-6-acetate as white crystals. Moreover, 180 mg of methyl ester of 8-methylsulfonyl-1,2,3,4-tetrahydro-2-trifluoromethylquinoline-6-acetic acid were obtained as white crystals.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 1 hours
  3. extractionthe reaction mixture was extracted with methylene chloride, which
  4. washwas washed with saturated aqueous sodium bicarbonate, with water and with saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationSolvent was distilled off
  7. customthe residue was purified by means of silica gel chromatography (development solvent; ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-ce458ce4d9b347ceba8a5fc0abe33f58
Source dataset
uspto-grants-1994_10
Patent number
US05359076

Reaction notes

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