Lithium Hydroxide → HCID 58648512, compound

HRID 1828524Notes

Reaction equation

HRID 1828524 reaction equation
[F:1]/[C:2](=[CH:8]\[C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][C:18]([CH2:20][CH2:21][C:22]3[S:23][CH:24]=[C:25]([CH:27]([CH3:29])[CH3:28])[N:26]=3)=[CH:19][C:12]2=[N:11][C:10]=1[N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)/[C:3]([O:5]CC)=[O:4].[OH-].[Li+]>O1CCCC1.CO.O>[F:1]/[C:2](=[CH:8]\[C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][C:18]([CH2:20][CH2:21][C:22]3[S:23][CH:24]=[C:25]([CH:27]([CH3:29])[CH3:28])[N:26]=3)=[CH:19][C:12]2=[N:11][C:10]=1[N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)/[C:3]([OH:5])=[O:4]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86588146HCID 86588146, compound2×

Product 1

HCID 58648512HCID 58648512, compoundYield 98.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The ethyl (Z)-2-fluoro-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (28 mg) obtained in (B) was dissolved in tetrahydrofuran (2 ml) and methanol (0.5 ml), added with a solution of lithium hydroxide(5 mg) in water (0.5 ml), and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with water and washed with ether. Then, the aqueous layer was made acidic with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (26 mg) as yellow powder.

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4224b12cb3ad42deaa47ef5bcc342d5e
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

Loading…