Lithium Hydroxide → HCID 49846452, compound

HRID 2360728Notes

Reaction equation

HRID 2360728 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4](/[CH:7]=[CH:8]/[CH2:9][C@:10]([OH:19])([CH3:18])[CH2:11][CH2:12][C:13]([F:17])=[C:14]([F:16])[F:15])[C@H:3]1[CH2:20][CH2:21][S:22][C:23]1[S:24][CH:25]=[C:26]([C:28]([O:30]C)=[O:29])[N:27]=1.[OH-].[Li+].S([O-])(O)(=O)=O.[K+]>COCCOC.O>[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4](/[CH:7]=[CH:8]/[CH2:9][C@:10]([OH:19])([CH3:18])[CH2:11][CH2:12][C:13]([F:17])=[C:14]([F:15])[F:16])[C@H:3]1[CH2:20][CH2:21][S:22][C:23]1[S:24][CH:25]=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 66978293HCID 66978293, compound

Product 1

HCID 49846452HCID 49846452, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Compound 16 (152 mg) was dissolved in 1,2-dimethoxyethane (2.0 mL)/water (1.0 mL), and lithium hydroxide (16.0 mg) was added thereto under ice cooling, followed by stirring at room temperature for 2 hr. The reaction solution was poured into a 5% aqueous solution of potassium hydrogen sulfate and extracted with ethyl acetate. The organic layer was washed with water and saturated brine; dried with anhydrous sodium sulfate; and concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→methanol:ethyl acetate=1:10) to obtain the title compound (127 mg, amorphous, viscous oil) having the following physical properties:

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationand concentrated
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→methanol:ethyl acetate=1:10)

Sources & evidence

ORD record
ord-4948b13faa0b454995fa18fc665d1fdf
Source dataset
uspto-grants-2014_04
Patent number
US08686160B2

Reaction notes

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