Lithium hydroxide, monohydrate → HCID 59235360, compound

HRID 2174331Notes

Reaction equation

HRID 2174331 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]([C:33](=[O:35])[CH3:34])=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:36][O:37]C(=O)C)(=O)C.O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C@H:8]2[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:36][OH:37])[O:7]2)=[CH:20][C:21]=1[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59557758HCID 59557758, compound

Product 1

HCID 59235360HCID 59235360, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-acetylbenzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (95 mg, 0.17 mmol) in a mixture of tetrahydrofuran/methanol/water (2.4 mL, 2:3:1) was added lithium hydroxide monohydrate (11.2 mg, 0.27 mmol). After stirring overnight at RT, volatiles were removed under reduced pressure. The residue was partitioned between water and ethyl acetate (3×), and the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated to give crude product 48 (68 mg), which was used in the next step without further purification. MS ESI: 407 [M+H]+, 451 [M+HCO2]−.

Workup

  1. customvolatiles were removed under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate (3×)
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d911f28d8e540cdb81dd3f7da9b5f06
Source dataset
uspto-grants-2015_06
Patent number
US09061060B2

Reaction notes

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