Water → Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-mesyloxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 1651384Notes

Reaction equation

HRID 1651384 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:25])=[C:16]([N:20]4[CH2:23][CH:22]([OH:24])[CH2:21]4)[C:17]=3[F:19])[C:12](=[O:26])[C:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:10]2)[CH2:8][CH2:7]1.O>N1C=CC=CC=1>[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:25])=[C:16]([N:20]4[CH2:21][CH:22]([O:24][S:1]([CH3:4])(=[O:3])=[O:2])[CH2:23]4)[C:17]=3[F:19])[C:12](=[O:26])[C:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:10]2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 15615453Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 15615454Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-mesyloxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

6.3 g (55.0 mmoles) of mesyl chloride are slowly added to a solution of 1.0 g (2.75 mmoles) of ethyl 1-cyclopropyl-6,8-difluoro-7-(3-hydroxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 50 ml of pyridine cooled to 0° C., and the reaction is maintained at 0° C. for 3 hours. The solution is added to a mixture of ice and water giving a precipitate which is filtered and washed with water. The solid is dried under vacuum yielding 0.9 g (73%) of ethyl 1-cyclopropyl-6,8-difluoro-7-(3-mesyloxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate melting at 191°-193° C.

Workup

  1. temperaturethe reaction is maintained at 0° C. for 3 hours
  2. filtrationis filtered
  3. washwashed with water
  4. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-2773d93c8eaf4269a05d5b789c545b6b
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

Loading…