Lithium hydroxide, monohydrate → HCID 53629635, compound

HRID 1011702Notes

Reaction equation

HRID 1011702 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:36]([O:38]C)=[O:37])[CH:5]=[N:6][C:7]=1[O:8][C:9]1[CH:14]=[C:13]([C:15]([NH:17][C:18]2[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=2)=[O:16])[CH:12]=[C:11]([O:24][C@@H:25]([CH3:35])[CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH:10]=1.O.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:36]([OH:38])=[O:37])[CH:5]=[N:6][C:7]=1[O:8][C:9]1[CH:14]=[C:13]([C:15]([NH:17][C:18]2[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=2)=[O:16])[CH:12]=[C:11]([O:24][C@@H:25]([CH3:35])[CH2:26][O:27][Si:28]([C:31]([CH3:33])([CH3:34])[CH3:32])([CH3:30])[CH3:29])[CH:10]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59127147HCID 59127147, compound

Product 1

HCID 53629635HCID 53629635, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-chloro-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 (1.2 g, 2.09 mmol) in THF (50 mL) was added a solution of lithium hydroxide monohydrate (0.219 g, 5.22 mmol) in water (30 mL). The mixture was allowed to stir under RT overnight. The THF was removed in vacuo and the resulting solution was partitioned between water (50 mL) and ethyl acetate (75 mL), and the ethyl acetate layer separated, washed with brine and dried (MgSO4). The aqueous layer was then adjusted to pH 7 by addition of 1N hydrochloric acid (5.2 mL) and partitioned between 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 (1.1 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 adjusted to pH 7 by addition of 1N hydrochloric acid (5.2 mL)
  7. custompartitioned between 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-58c70477556941b9b5b886ef41243570
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

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