Lithium Hydroxide → HCID 49846452, compound

HRID 1960057Notes

Reaction equation

HRID 1960057 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-83f060edc6e643d28decf5f3b4dbf779
Source dataset
uspto-grants-2013_04
Patent number
US08410281B2

Reaction notes

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