Sodium hydride → Moxifloxacin difluoro methoxy ethyl ester

HRID 1770111Notes

Reaction equation

HRID 1770111 reaction equation
[CH3:1][O:2][C:3]1[C:4](F)=[C:5]([CH:19]=[C:20]([F:23])[C:21]=1[F:22])[C:6]([C:8](=[CH:14][NH:15][CH:16]1[CH2:18][CH2:17]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7].[H-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[C:21]([F:22])=[C:20]([F:23])[CH:19]=[C:5]2[C:4]=1[N:15]([CH:16]1[CH2:18][CH2:17]1)[CH:14]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:6]2=[O:7]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178471878HCID 178471878, compound

Product 1

HCID 10758239Moxifloxacin difluoro methoxy ethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2-(3-methoxy-2,4,5-trifluorobenzoyl)-3-cyclopropylaminoacrylate (440 mg, 1.29 mmol) in anhydrous tetrahydrofuran (15 mL) at 0° C. was added sodium hydride (62 mg, 1.5 mmol, 1.1 equiv, 60% in mineral oil). The reaction mixture was allowed to stir at 50° C. for 12 hours. The mixture was cooled to room temperature and filtered. The mother liquor was concentrated and a white precipitate formed. The material was collected by suction filtration and air-dried to give 312 mg, 75% yield of a pure white solid, m.p. 178°-181° C.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe mother liquor was concentrated
  4. customa white precipitate formed
  5. filtrationThe material was collected by suction filtration
  6. customair-dried

Sources & evidence

ORD record
ord-5d49d6c7b08743c19637ed2231c32785
Source dataset
uspto-grants-1995_01
Patent number
US05385913

Reaction notes

Loading…