Lithium Hydroxide → 2-((3S)-6-((1R)-4-(3-Cyano-2-methylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 237512Notes

Reaction equation

HRID 237512 reaction equation
[Li+].[OH-].[C:3]([C:5]1[C:6]([CH3:36])=[C:7]([C:11]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]3[C:12]=2[CH2:13][CH2:14][C@H:15]3[O:21][C:22]2[CH:35]=[CH:34][C:25]3[C@H:26]([CH2:29][C:30]([O:32]C)=[O:31])[CH2:27][O:28][C:24]=3[CH:23]=2)[CH:8]=[CH:9][CH:10]=1)#[N:4]>O1CCCC1.O.CO>[C:3]([C:5]1[C:6]([CH3:36])=[C:7]([C:11]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]3[C:12]=2[CH2:13][CH2:14][C@H:15]3[O:21][C:22]2[CH:35]=[CH:34][C:25]3[C@H:26]([CH2:29][C:30]([OH:32])=[O:31])[CH2:27][O:28][C:24]=3[CH:23]=2)[CH:8]=[CH:9][CH:10]=1)#[N:4]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86697173Methyl 2-((3S)-6-((1R)-4-(3-cyano-2-methylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 866971742-((3S)-6-((1R)-4-(3-Cyano-2-methylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

LiOH×H2O (131 mg) is added to a solution of methyl 2-((3S)-6-((1R)-4-(3-cyano-2-methylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (119 mg) in tetrahydrofuran (1 mL), water (1 mL) and methanol (1 mL) at room temperature. The mixture is stirred at room temperature for 12 hours. The mixture is concentrated, cooled to 0° C., diluted with water and acidified with 4 M aqueous HCl solution. The resulting mixture is extracted with dichloromethane. The organic phase is dried (MgSO4). The solvent is evaporated to give the title compound. Yield: 103 mg; LC (method 20): tR=6.30 min; Mass spectrum (ESI−): m/z=442 [M−H]−.

Workup

  1. concentrationThe mixture is concentrated
  2. temperaturecooled to 0° C.
  3. additiondiluted with water
  4. extractionThe resulting mixture is extracted with dichloromethane
  5. dry with materialThe organic phase is dried (MgSO4)
  6. customThe solvent is evaporated

Sources & evidence

ORD record
ord-46160cd5e42c4161a41619332da8cb59
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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