Hydrochloric Acid → HCID 54326695, compound

HRID 893580Notes

Reaction equation

HRID 893580 reaction equation
[Cl:1][C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]2)=[C:4]([F:21])[CH:5]=[C:6]2[C:11]=1[N:10]1[CH:12]([CH3:14])[S:13][C:9]1=[C:8]([C:15]([O:17]CC)=[O:16])[C:7]2=[O:20].[OH-].[K+].C(O)(C)(C)C.Cl>O>[Cl:1][C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@H:24]([N:27]([CH3:28])[CH3:29])[CH2:23]2)=[C:4]([F:21])[CH:5]=[C:6]2[C:11]=1[N:10]1[CH:12]([CH3:14])[S:13][C:9]1=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 54530966HCID 54530966, compound

Product 1

HCID 54326695HCID 54326695, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.44 g of ethyl 8-chloro-7-((S)-3-dimethylamino-1-pyrrolidinyl)-6-fluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate, 0.33 g of 85% potassium hydroxide, 2.0 ml of tert-butanol and 6.0 ml of water was heated at 60° C. for 1 hour with stirring. After cooling, the reaction mixture was neutralized with 10% hydrochloric acid, and evaporated. To the residue, water was added and the residue was extracted with chloroform. The extract was dried and acidified with ethanolic hydrochloride. The solution was evaporated and to the residue was added small amount of methanol. The precipitate was collected by filtration and dissolved with water. The solution was neutralized with 10% aqueous sodium hydroxide and extracted with chloroform. The extract was dried, evaporated and recrystallized from a mixture of chloroform and iso-propanol to give 0.25 g of the desired compound as pale yellow crystals, m.p. 161°-162° C.

Workup

  1. temperatureAfter cooling
  2. customevaporated
  3. additionTo the residue, water was added
  4. extractionthe residue was extracted with chloroform
  5. customThe extract was dried
  6. customThe solution was evaporated and to the residue
  7. additionwas added small amount of methanol
  8. filtrationThe precipitate was collected by filtration
  9. dissolutiondissolved with water
  10. extractionextracted with chloroform
  11. customThe extract was dried
  12. customevaporated
  13. customrecrystallized from a mixture of chloroform and iso-propanol

Sources & evidence

ORD record
ord-09cfb5d2dc0a478487f3111466b0e2ce
Source dataset
uspto-grants-1992_06
Patent number
US05126337

Reaction notes

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