Lithium Hydroxide → HCID 44249133, compound

HRID 1891426Notes

Reaction equation

HRID 1891426 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 vigorously stirred slution of the product from step e) (307 g) in THF (3 L) was added a solution of lithium hydroxide (148 g) in water (0.6 L) and the reaction stirred at RT for 45 min. Aqueous 20% brine solution (2.5L) was added and the layers separated. The organic fraction was concentrated in vacuo, the residue re-dissolved in water (6 L) and the stirred mixture acidified to pH 1 with conc HCl. 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 for 48 h at 40° C. to give the title product in crude form (259 g).

Workup

  1. customthe layers separated
  2. concentrationThe organic fraction was concentrated in vacuo
  3. dissolutionthe residue re-dissolved in water (6 L)
  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 for 48 h at 40° C.

Sources & evidence

ORD record
ord-95dfd80dd3544b499b9d66c045659ffb
Source dataset
uspto-grants-2013_08
Patent number
US08507544B2

Reaction notes

Loading…