Lithium hydroxide, monohydrate → HCID 89442891, compound

HRID 1474616Notes

Reaction equation

HRID 1474616 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]([O:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH:37]=[N:38][O:39][CH3:40])=[CH:31][CH:30]=2)[CH:22]=1)(=O)C.O.[OH-].[Li+]>C1COCC1.CO.O>[CH3:40][O:39][N:38]=[CH:37][CH2:36][O:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][C:23]2[CH:22]=[C:21]([C@H:6]3[C@H:5]([OH:4])[C@@H:10]([OH:11])[C@H:9]([OH:15])[C@@H:8]([O:19][CH3:20])[O:7]3)[CH:26]=[CH:25][C:24]=2[Cl:27])=[CH:30][CH:31]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 131732772HCID 131732772, compound

Product 1

HCID 89442891HCID 89442891, compoundYield 64.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (140 mg, 0.242 mmol) in THF (0.8 mL), methanol (1.2 mL) and water (0.4 mL) was added lithium hydroxide monohydrate (20.4 mg, 0.485 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, 1:9 MeOH:DCM) to provide the title compound (70 mg, 64.2%).

Workup

  1. customVolatiles were evaporated in vacuo
  2. customthe residue obtained
  3. customwas purified by column chromatography (silica gel, 1:9 MeOH:DCM)

Sources & evidence

ORD record
ord-255a53f8baf94774ab2fb2db4ac947c0
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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