Sodium Hydroxide → HCID 86697377, compound

HRID 237708Notes

Reaction equation

HRID 237708 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:14][N:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH2:12]2)[CH:7]=[C:6]([CH3:19])[C:5]=1[C:20]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]2[C:21]=1[CH2:22][CH2:23][C@H:24]2[O:30][C:31]1[CH:44]=[CH:43][C:34]2[C@H:35]([CH2:38][C:39]([O:41]C)=[O:40])[CH2:36][O:37][C:33]=2[CH:32]=1>O.C(O)(C)C>[CH3:3][C:4]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:14][N:13]([S:15]([CH3:18])(=[O:16])=[O:17])[CH2:12]2)[CH:7]=[C:6]([CH3:19])[C:5]=1[C:20]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]2[C:21]=1[CH2:22][CH2:23][C@H:24]2[O:30][C:31]1[CH:44]=[CH:43][C:34]2[C@H:35]([CH2:38][C:39]([OH:41])=[O:40])[CH2:36][O:37][C:33]=2[CH:32]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86697378HCID 86697378, compound2×

Product 1

HCID 86697377HCID 86697377, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Aqueous NaOH solution (1 M; 39 μL) is added to a solution of methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(1-(methylsulfonyl)azetidin-3-yloxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (Intermediate 28-1, 50 mg) in water (0.5 mL) and isopropanol (0.5 mL) at ambient temperature. The mixture is stirred at ambient temperature for 12 hours. The mixture is concentrated and acidified with 10% aqueous citric acid solution. The resulting mixture is extracted with dichloromethane, and the extract dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:30→0:100) to give the title compound. Yield: 35 mg.

Workup

  1. concentrationThe mixture is concentrated
  2. extractionThe resulting mixture is extracted with dichloromethane
  3. dry with materialthe extract dried (MgSO4)
  4. customThe solvent is evaporated
  5. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:30→0:100)

Sources & evidence

ORD record
ord-716cfd18849d4872887d9e9046c6af06
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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