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

HRID 237714Notes

Reaction equation

HRID 237714 reaction equation
[Li+].[OH-].[CH3:3][C:4]1[CH:9]=[C:8]([C:10](=[O:13])[NH:11][CH3:12])[CH:7]=[C:6]([CH3:14])[C:5]=1[C:15]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]2[C:16]=1[CH2:17][CH2:18][C@H:19]2[O:25][C:26]1[CH:39]=[CH:38][C:29]2[C@H:30]([CH2:33][C:34]([O:36]C)=[O:35])[CH2:31][O:32][C:28]=2[CH:27]=1>C(O)C.O>[CH3:3][C:4]1[CH:9]=[C:8]([C:10](=[O:13])[NH:11][CH3:12])[CH:7]=[C:6]([CH3:14])[C:5]=1[C:15]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]2[C:16]=1[CH2:17][CH2:18][C@H:19]2[O:25][C:26]1[CH:39]=[CH:38][C:29]2[C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:31][O:32][C:28]=2[CH:27]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86697181Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(methylcarbamoyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 866973852-((S)-6-((R)-4-(2,6-Dimethyl-4-(methylcarbamoyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

LiOH×H2O (3 mg) is added to a solution of methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(methylcarbamoyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (20 mg) in ethanol (0.77 mL) and water (0.5 mL) and the mixture is stirred for 24 hours at room temperature. After concentration the mixture is diluted with water, acidified with aqueous citric acid solution and extracted with dichloromethane. The organic phase is dried (MgSO4) and the residue chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→60:40) to give the title compound. Yield 11 mg, LC (method 20): tR=5.54 min; Mass spectrum (ESI+): m/z=490 [M+H]+.

Workup

  1. concentrationAfter concentration the mixture
  2. additionis diluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase is dried (MgSO4)
  5. customthe residue chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→60:40)

Sources & evidence

ORD record
ord-a2213dee2242415e877a4e81fcc8e849
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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