Lithium hydroxide, monohydrate → HCID 117762022, compound

HRID 1474629Notes

Reaction equation

HRID 1474629 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH:34]=[N:35][O:36][CH3:37])=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:38][O:39]C(=O)C)(=O)C.O.[OH-].[Li+]>C1COCC1.CO.O>[CH3:37][O:36][N:35]=[CH:34][CH2:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][C:21]2[CH:20]=[C:19]([C@H:8]3[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:38][OH:39])[O:7]3)[CH:24]=[CH:23][C:22]=2[Cl:25])=[CH:32][CH:31]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 89442828HCID 89442828, compound

Product 1

HCID 117762022HCID 117762022, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(2-(methoxyimino)ethyl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (80 mg, 0.132 mmol) in THF (0.5 mL), methanol (0.7 mL) and water (0.3 mL) was added lithium hydroxide monohydrate (11 mg, 0.26 mmol) at 0° C. The reaction was stirred at r.t. for 1 h. Volatiles were evaporated in vacuo and the residue obtained was purified by column chromatography (silica gel, 0.5:9.5 MeOH:DCM) to provide the title compound (44 mg, 77%).

Workup

  1. customVolatiles were evaporated in vacuo
  2. customthe residue obtained
  3. customwas purified by column chromatography (silica gel, 0.5:9.5 MeOH:DCM)

Sources & evidence

ORD record
ord-fd96d00ae49d435d9ad0e821f11bac94
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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