Hydrochloric Acid → HCID 66657767, compound

HRID 420577Notes

Reaction equation

HRID 420577 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH:19]([CH3:21])[N:18]([C:22]3[S:23][C:24]4[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:25]=4[N:26]=3)[CH:17]([CH3:35])[CH2:16]2)[CH:6]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:36])=[O:2])=[CH:6][C:7]=1[O:12][CH2:13][CH2:14][N:15]1[CH2:20][CH:19]([CH3:21])[N:18]([C:22]2[S:23][C:24]3[CH:30]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:28]=[CH:27][C:25]=3[N:26]=2)[CH:17]([CH3:35])[CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66658330HCID 66658330, compound

Product 1

HCID 66657767HCID 66657767, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [4-chloro-3-[2-[3,5-dimethyl-4-(6-trifluoromethyl benzothiazole-2-yl)piperazine-1-yl]ethoxy]phenyl]acetic acid methyl ester (178 mg), 2N aqueous sodium hydroxide (0.66 mL), tetrahydrofuran (2 mL) and methanol (2 mL) was stirred at room temperature for 2 hours. The mixture was neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (83 mg). Yield: 48%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-d3c644a1d2ec4df0b01a1f54aa88afe0
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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