Water → HCID 54511641, compound

HRID 893579Notes

Reaction equation

HRID 893579 reaction equation
[Cl:1][C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@H:24]([NH:27]C(=O)C(F)(F)F)[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.O>C(O)(=O)C>[NH2:27][C@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([Cl:1])=[C:11]3[C:6]([C:7](=[O:20])[C:8]([C:15]([OH:17])=[O:16])=[C:9]4[S:13][CH:12]([CH3:14])[N:10]43)=[CH:5][C:4]=2[F:21])[CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 22844776HCID 22844776, compound

Product 1

HCID 54511641HCID 54511641, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.90 g of ethyl 8-chloro-6-fluoro-1-methyl-4-oxo-7-((S)-3-trifluoroacetylamino-1-pyrrolidinyl)-1H,4H-[1,3]-thiazeto[3,2-a]quinoline-3-carboxylate, 1.23 g of 85% potassium hydroxide, 6.0 ml of tert-butanol and 12 ml of water was stirred at room temperature for 5 hours. The reaction mixture was neutralized with aqueous acetic acid. The precipitate was collected by filtration and recrystallized from water to give 0.51 g of yellow crystals, which were consistent with that of Example 29.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customrecrystallized from water

Sources & evidence

ORD record
ord-e5fddde5e7a84953bb7c9c04d390e5e7
Source dataset
uspto-grants-1992_06
Patent number
US05126337

Reaction notes

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