Lithium Hydroxide → HCID 44249133, compound

HRID 1891427Notes

Reaction equation

HRID 1891427 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][C@@H:25]([CH3:30])[C:26]([O:28]C)=[O:27])[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C:11]1([CH3:16])[CH3:15])=[O:9].[OH-].[Li+]>C1COCC1.O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][C@@H:25]([CH3:30])[C:26]([OH:28])=[O:27])[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C:11]1([CH3:16])[CH3:15])=[O:9]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 25152882HCID 25152882, compound

Product 1

HCID 44249133HCID 44249133, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the product from example 3 step e) (21.4 g) in THF (200 mL) was added a solution of lithium hydroxide (10.35 g) in water (40 mL) with vigorous stirring. After 45 min, aqueous 20% brine solution (160 mL) was added and the layers separated. The organic fraction was concentrated in vacuo, the residue re-dissolved in water (400 mL) and acidified to pH 2 with conc HCl whilst stirring. The resulting precipitate was filtered and washed with portions of water until the filtrate was pH 6. Iso-hexane was eluted through the filter cake to remove excess water and the solid was dried in a vacuum oven at 40° C. to give the title product in crude form (˜20 g). A portion of this solid (1 g ) was recrystallised by heating to reflux in MeCN (5 mL) until dissolution, followed by cooling to RT, stirring for 16 h and collection of the resulting solid and drying in vacuo to afford the title product (0.759 g).

Workup

  1. customthe layers separated
  2. concentrationThe organic fraction was concentrated in vacuo
  3. dissolutionthe residue re-dissolved in water (400 mL)
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with portions of water until the filtrate
  6. washIso-hexane was eluted through the filter cake
  7. customto remove excess water
  8. customthe solid was dried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-f8e54d2b72aa40b8802c89a8cda909c9
Source dataset
uspto-grants-2013_08
Patent number
US08507544B2

Reaction notes

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