Hydrochloric Acid → HCID 57719918, compound

HRID 1985300Notes

Reaction equation

HRID 1985300 reaction equation
[CH:1]([O:4][CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)=[O:21])[CH:13]=1)[C:6]([O:8]CC)=[O:7])([CH3:3])[CH3:2].C(O)C.[OH-].[Na+].Cl>O.C(OCC)(=O)C.[Cl-].[NH4+]>[CH:1]([O:4][CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][C:20]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=2)=[O:21])[CH:13]=1)[C:6]([OH:8])=[O:7])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 57719926HCID 57719926, compound

Product 1

HCID 57719918HCID 57719918, compoundYield 18.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To 149 mg of Ethyl 2-isopropoxy-3-{3-[({[4-(trifluoromethyl)anilino]carbonyl}-oxy)methyl]phenyl}propanoate were added 4 ml of ethanol and 1.0 ml of 5N sodium hydroxide aqueous solution, and the mixture was stirred at room temperature for 20 hours. After the reaction solution was diluted with water, pH was adjusted to 5 with 5N hydrochloric acid, and the solution was diluted with ethyl acetate and saturated aqueous ammonium chloride. The organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography, to give 26 mg of the title compound.

Workup

  1. washThe organic layer was washed with saturated aqueous ammonium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3c9445bbfed44f5c947c63127cc83528
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

Loading…