Lithium Hydroxide → HCID 71737973, compound

HRID 237715Notes

Reaction equation

HRID 237715 reaction equation
[Li+].[OH-].[CH3:3][C:4]1[CH:9]=[C:8]([C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:11])[CH:7]=[C:6]([CH3:18])[C:5]=1[C:19]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]2[C:20]=1[CH2:21][CH2:22][C@H:23]2[O:29][C:30]1[CH:43]=[CH:42][C:33]2[C@H:34]([CH2:37][C:38]([O:40]C)=[O:39])[CH2:35][O:36][C:32]=2[CH:31]=1>C(O)C.O>[CH3:3][C:4]1[CH:9]=[C:8]([C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[O:11])[CH:7]=[C:6]([CH3:18])[C:5]=1[C:19]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]2[C:20]=1[CH2:21][CH2:22][C@H:23]2[O:29][C:30]1[CH:43]=[CH:42][C:33]2[C@H:34]([CH2:37][C:38]([OH:40])=[O:39])[CH2:35][O:36][C:32]=2[CH:31]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86697185HCID 86697185, compound

Product 1

HCID 71737973HCID 71737973, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

LiOH×H2O (4.1 mg) is added to a solution of methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(morpholine-4-carbonyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (55 mg) in ethanol (1.9 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 concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50) to give the title compound. Yield 10 mg, LC (method 20): tR=5.73 min; Mass spectrum (ESI+): m/z=546 [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. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50)

Sources & evidence

ORD record
ord-b78c75751a074c6b8525339927e351e2
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

Loading…