tert-Butanol → HCID 10452425, compound

HRID 1085784Notes

Reaction equation

HRID 1085784 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:19])[C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[N:8]1[CH:20]([CH3:22])[S:21][C:7]1=[C:6]([C:23]([O:25]CC)=[O:24])[C:5]2=[O:28].[OH-].[K+].C(O)(C)(C)C>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:19])[C:11]=1[N:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1)[N:8]1[CH:20]([CH3:22])[S:21][C:7]1=[C:6]([C:23]([OH:25])=[O:24])[C:5]2=[O:28]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 10476611HCID 10476611, compound

Product 1

HCID 10452425HCID 10452425, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 0.5 g of ethyl 6,8-difluoro-1-methyl-7-(4-methyl-1-piperazinyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate was added 10 ml of 5% solution of potassium hydroxide in 3:1 mixture of tert-butanol and water and stirred at 60° C. for 30 minutes. tert-Butanol was evaporated therefrom in vacuo, the residue was neutralized with acetic acid, extracted with a 3:1 mixture of chloroform and methanol, the extract was washed with saturated sodium chloride solution, dried over magnesium sulfate, the solvent was evaporated therefrom, and the residue was subjected to a silica gel column chromatography (30 g of Wakogel C-300 being used) and eluted with chloroform-methanol (10:1) to give 0.18 g of desired product, m.p. 238° C. (decompn.).

Workup

  1. customtert-Butanol was evaporated
  2. extractionextracted with a 3:1 mixture of chloroform and methanol
  3. washthe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. washeluted with chloroform-methanol (10:1)

Sources & evidence

ORD record
ord-8bf4ab4560ec4fb19e846110fe2b8bbf
Source dataset
uspto-grants-1991_04
Patent number
US05011831

Reaction notes

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