Lithium hydroxide, monohydrate → HCID 53629692, compound

HRID 1011821Notes

Reaction equation

HRID 1011821 reaction equation
O.[OH-].[Li+].CC([Si](C)(C)[O:9][C:10]1[CH:11]=[C:12]([CH:23]=[C:24]([O:26][C@@H:27]([CH3:37])[CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH:25]=1)[C:13]([NH:15][C:16]1[CH:21]=[N:20][C:19]([CH3:22])=[CH:18][N:17]=1)=[O:14])(C)C>O.C1COCC1>[CH3:34][C:33]([Si:30]([CH3:31])([CH3:32])[O:29][CH2:28][C@@H:27]([O:26][C:24]1[CH:23]=[C:12]([CH:11]=[C:10]([OH:9])[CH:25]=1)[C:13]([NH:15][C:16]1[CH:21]=[N:20][C:19]([CH3:22])=[CH:18][N:17]=1)=[O:14])[CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 536296933-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-[((1S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-methylethyl)oxy]-N-(5-methylpyrazin-2-yl)benzamide

Product 1

HCID 53629692HCID 53629692, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (0.38 g, 9.12 mol) in water (20 mL) 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-(5-methylpyrazin-2-yl)benzamide (1.94 g, 3.65 mol) in THF (40 mL) and stirred at RT for 20 hours. The THF was removed in vacuo and the aqueous layer was adjusted to pH7. Ethyl acetate (50 mL) and water (50 mL) were added then the aqueous layer re-extracted into ethyl acetate (50 mL) and the combined organics washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and reduced in vacuo. The crude material was chromatographed on silica, eluting with 20-50% ethyl acetate in isohexane, to give the desired material as a white solid (0.8 g). 1H NMR δ (CDCl3): 0.04 (s, 3H), 0.08 (s, 3H), 0.87 (s, 9H), 1.30 (d, 3H), 2.56 (s, 3H), 3.65-3.81 (m, 2H), 4.46-4.51 (m, 1H), 5.63 (s, 1H), 6.63 (t, 1H), 6.98 (t, 1H), 7.04 (t, 1H), 8.15 (s, 1H), 8.41 (s, 1H), 9.57 (s, 1H); m/z 418 (M+H)+

Workup

  1. customThe THF was removed in vacuo
  2. additionEthyl acetate (50 mL) and water (50 mL) were added
  3. extractionthe aqueous layer re-extracted into ethyl acetate (50 mL)
  4. washthe combined organics washed with water (50 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe crude material was chromatographed on silica
  8. washeluting with 20-50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-f2172325c2cf4d7181b68fe4d8a24880
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

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