Hydrochloric Acid → HCID 10311939, compound

HRID 1985200Notes

Reaction equation

HRID 1985200 reaction equation
C([O:3][C:4](=[O:42])[C:5]([CH3:41])([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>C(O)C>[CH3:41][C:5]([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH:16]2[CH2:20][N:19]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[C:18](=[O:32])[N:17]2[CH3:33])=[CH:11][CH:12]=1)[C:4]([OH:42])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 102399822-Methyl-3-(4-{2-[3-methyl-2-oxo-1-(3-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester

Product 1

HCID 10311939HCID 10311939, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the esters obtained from Step A (270 mg) in absolute ethanol (4.5 ml) is added 5N NaOH (1.9 ml, 9.5 mmol), and the mixture stirred for 20 hours at ambient temperature. The mixture is poured into 1N HCl, then extracted with ethyl acetate (2×20 ml). The combined ethyl acetate extracts were washed with water, brine, dried (Na2SO4), and concentrated to an oil which is purified is purified by flash chromatography on a Biotage silica cartridge (gradient elution, 3:1 hexanes:ethyl acetate to 1:2 hexanes:ethyl acetate to yield a foam (78 mg).

Workup

  1. extractionextracted with ethyl acetate (2×20 ml)
  2. washThe combined ethyl acetate extracts were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to an oil which
  5. customis purified
  6. customis purified by flash chromatography on a Biotage silica cartridge (
  7. washgradient elution, 3:1 hexanes

Sources & evidence

ORD record
ord-9902d53b004c4a5da5c88617786dbcc5
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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