Hydrochloric Acid → tert-Butyl (E)-3-{2-(3-hydroxypiperidino)-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

HRID 1828489Notes

Reaction equation

HRID 1828489 reaction equation
C([O:3][CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[N:11]=[C:12]3[CH:29]=[C:28](/[CH:30]=[CH:31]/[C:32]4[S:33][CH:34]=[C:35]([CH:37]([CH3:39])[CH3:38])[N:36]=4)[CH:27]=[CH:26][N:13]3[C:14](=[O:25])[C:15]=2/[CH:16]=[CH:17]/[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:5]1)=O.[OH-].[Na+].Cl>CO>[OH:3][CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[N:11]=[C:12]3[CH:29]=[C:28](/[CH:30]=[CH:31]/[C:32]4[S:33][CH:34]=[C:35]([CH:37]([CH3:39])[CH3:38])[N:36]=4)[CH:27]=[CH:26][N:13]3[C:14](=[O:25])[C:15]=2/[CH:16]=[CH:17]/[C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86588120tert-Butyl (E)-3-{2-(3-formyloxypiperidino)-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoate2×

Product 1

HCID 86588119tert-Butyl (E)-3-{2-(3-hydroxypiperidino)-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The tert-butyl (E)-3-{2-(3-formyloxypiperidino)-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (184 mg, 0.334 mmol) obtained in (G) was dissolved in methanol (3.0 ml), added with 1 N aqueous sodium hydroxide (1.0 ml), and then the mixture was stirred at room temperature for 10 minutes. The reaction mixture was added with 1 N hydrochloric acid (1.0 ml) and extracted with chloroform. 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 (n-hexane:ethyl acetate=2:1→2:1→1:2, v/v) to obtain the title compound (174 mg, 100%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane

Sources & evidence

ORD record
ord-08bb8696a551434ab91044354cb266df
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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