Lithium Hydroxide → HCID 86697384, compound

HRID 237713Notes

Reaction equation

HRID 237713 reaction equation
[Li+].[OH-].[CH3:3][N:4]([CH3:40])[C:5]([C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]3[C:15]=2[CH2:16][CH2:17][C@H:18]3[O:24][C:25]2[CH:38]=[CH:37][C:28]3[C@H:29]([CH2:32][C:33]([O:35]C)=[O:34])[CH2:30][O:31][C:27]=3[CH:26]=2)=[C:9]([CH3:39])[CH:8]=1)=[O:6]>C(O)C.O>[CH3:40][N:4]([CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH3:39])[C:10]([C:14]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]3[C:15]=2[CH2:16][CH2:17][C@H:18]3[O:24][C:25]2[CH:38]=[CH:37][C:28]3[C@H:29]([CH2:32][C:33]([OH:35])=[O:34])[CH2:30][O:31][C:27]=3[CH:26]=2)=[C:11]([CH3:13])[CH:12]=1)=[O:6]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86697178HCID 86697178, compound

Product 1

HCID 86697384HCID 86697384, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

LiOH×H2O (11 mg) is added to a solution of methyl 2-((S)-6-((R)-4-(4-(dimethylcarbamoyl)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (70 mg) in ethanol (2.6 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. After concentration the mixture is partitioned between dichloromethane and citric acid. The organic phase is dried (MgSO4) and concentrated to give the title compound. Yield 21 mg, LC (method 20): tR=5.87 min; Mass spectrum (ESI+): m/z=504 [M+H]+.

Workup

  1. concentrationAfter concentration the mixture
  2. additionis diluted with water
  3. extractionextracted with dichloromethane
  4. concentrationAfter concentration the mixture
  5. customis partitioned between dichloromethane and citric acid
  6. dry with materialThe organic phase is dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2e98ce25d7d348ba8de5b5a2e546b28d
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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