Lithium Hydroxide → HCID 10049043, compound

HRID 2111976Notes

Reaction equation

HRID 2111976 reaction equation
[O:1]=[C:2]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1)[CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][CH2:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12].[OH-].[Li+]>C1COCC1.O>[O:1]=[C:2]([NH:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=1)[CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][CH2:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68871490HCID 68871490, compound

Product 1

HCID 10049043HCID 10049043, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-{[3-(2-oxo-2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]methyl}-benzoate (82 mg, 0.18 mmol) in THF (2 ml) was cooled in an ice-bath. Lithium hydroxide (8.6 mg, 0.36 mmol) in water (1 ml) was dropped in. The cooling-bath was then removed and the mixture was stirred for 7 days and then evaporated in vacuum to remove THF. The residue was acidified with 1% hydrochloric acid, pH˜3, and extracted with ethyl acetate. The organic phase was dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM and MeOH/DCM (1:99, then 2:98) as eluant gave 20 mg the desired product, yield 22.5% (two steps).

Workup

  1. customThe cooling-bath was then removed
  2. customevaporated in vacuum
  3. customto remove THF
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried (magnesium sulphate)
  6. customevaporated

Sources & evidence

ORD record
ord-a0041058c7c5411f9fbde6d58e8f3eac
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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