Lithium hydroxide, monohydrate → HCID 59127134, compound

HRID 1990118Notes

Reaction equation

HRID 1990118 reaction equation
O.[OH-].[Li+].CC([Si](C)(C)[O:9][C:10]1[CH:11]=[C:12]([CH:21]=[C:22]([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:23]=1)[C:13]([NH:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1)=[O:14])(C)C>C1COCC1>[CH3:32][C:31]([Si:28]([CH3:30])([CH3:29])[O:27][CH2:26][C@@H:25]([O:24][C:22]1[CH:21]=[C:12]([CH:11]=[C:10]([OH:9])[CH:23]=1)[C:13]([NH:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1)=[O:14])[CH3:35])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 536296183-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-1,3-thiazol-2-ylbenzamide

Product 1

HCID 59127134HCID 59127134, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of lithium hydroxide monohydrate (0.304 g, 7.25 mmol) was added to a solution of 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-1,3-thiazol-2-ylbenzamide (1.552 g, 2.90 mmol) in THF (40 mL) and stirred at RT overnight. The THF was removed in vacuo and the residual solution adjusted to pH 7 by addition of 1N hydrochloric acid (7.25 mL). A gum formed, and the solution was filtered and the gum dissolved in methanol. The filtrate was partitioned with ethyl acetate (75 mL) and the organics washed with brine, dried (MgSO4), combined with the methanol solution and evaporated to a residue which was chromatographed on silica, eluting with 40% ethyl acetate in isohexane, to give the required product (0.865 g)

Workup

  1. customThe THF was removed in vacuo
  2. additionthe residual solution adjusted to pH 7 by addition of 1N hydrochloric acid (7.25 mL)
  3. customA gum formed
  4. filtrationthe solution was filtered
  5. dissolutionthe gum dissolved in methanol
  6. customThe filtrate was partitioned with ethyl acetate (75 mL)
  7. washthe organics washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated to a residue which
  10. customwas chromatographed on silica
  11. washeluting with 40% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-cbd68c72f94c4c62a60d2d3b04f1143e
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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