Lithium hydroxide, monohydrate → HCID 53629631, compound

HRID 1175866Notes

Reaction equation

HRID 1175866 reaction equation
O.[OH-].[Li+].[CH3:4][C:5]([Si:8]([CH3:41])([CH3:40])[O:9][CH2:10][C@@H:11]([O:13][C:14]1[CH:15]=[C:16]([O:29][C:30]2[N:35]=[CH:34][C:33]([C:36]([O:38]C)=[O:37])=[CH:32][CH:31]=2)[CH:17]=[C:18]([C:20]([NH:22][C:23]2[CH:27]=[CH:26][N:25]([CH3:28])[N:24]=2)=[O:21])[CH:19]=1)[CH3:12])([CH3:7])[CH3:6]>O.C1COCC1>[CH3:4][C:5]([Si:8]([CH3:41])([CH3:40])[O:9][CH2:10][C@@H:11]([O:13][C:14]1[CH:15]=[C:16]([O:29][C:30]2[N:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32][CH:31]=2)[CH:17]=[C:18]([C:20]([NH:22][C:23]2[CH:27]=[CH:26][N:25]([CH3:28])[N:24]=2)=[O:21])[CH:19]=1)[CH3:12])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59127148HCID 59127148, compound

Product 1

HCID 53629631HCID 53629631, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (0.10 g, 4.17 mmol) in water (15 mL) was added to a solution of methyl 6-[(3-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenyl)oxy]pyridine-3-carboxylate (0.90 g, 1.67 mmol) in THF (30 mL). The mixture was allowed to stir at RT overnight. The THF was removed in vacuo and the resulting solution was partitioned between water (50 mL) and ethyl acetate (75 mL), then the ethyl acetate layer separated, washed with brine and dried (MgSO4). The aqueous layer was then taken to pH 7 by addition of 1N hydrochloric acid (5.2 mL) and extracted with ethyl acetate (75 mL). The ethyl acetate layer was separated, washed with brine and dried (MgSO4). The ethyl acetate layers were combined and evaporated to give the required product (0.84 g).

Workup

  1. customThe THF was removed in vacuo
  2. customthe resulting solution was partitioned between water (50 mL) and ethyl acetate (75 mL)
  3. customthe ethyl acetate layer separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. additionThe aqueous layer was then taken to pH 7 by addition of 1N hydrochloric acid (5.2 mL)
  7. extractionextracted with ethyl acetate (75 mL)
  8. customThe ethyl acetate layer was separated
  9. washwashed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-2beb3778ce74486b81deb51088849a53
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

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