Sodium hydride → HCID 67920079, compound

HRID 1382218Notes

Reaction equation

HRID 1382218 reaction equation
[H-].[Na+].[CH:3]1([N:6]2[C:15]3[C:10](=[CH:11][C:12]([F:24])=[C:13]([N:17]4[CH2:21][CH2:20][CH2:19][C@H:18]4[CH2:22][OH:23])[C:14]=3F)[C:9](=[O:25])[C:8]([C:26]([OH:28])=[O:27])=[CH:7]2)[CH2:5][CH2:4]1.[H][H]>CN(C=O)C>[CH:3]1([N:6]2[C:15]3[C:14]4[O:23][CH2:22][C@@H:18]5[CH2:19][CH2:20][CH2:21][N:17]5[C:13]=4[C:12]([F:24])=[CH:11][C:10]=3[C:9](=[O:25])[C:8]([C:26]([OH:28])=[O:27])=[CH:7]2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53739370HCID 53739370, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67920079HCID 67920079, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.2 mg of a 55% sodium hydride dispersion were added to a solution of 0.364 g (1 mmol) of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[(S)-2-hydroxymethyl-1-pyrrolidinyl]-4-oxoquinoline-3-carboxylic acid in 8 ml of DMF. After completion of the hydrogen evolution, the mixture was stirred at 140° C. for 35 minutes, the solvent was evaporated, the residue was taken up in water, adjusted to pH 6 with glacial acetic acid and suction filtered. Crystallization from ethanol gave (S)-4-cyclopropyl-11-fluoro-1,4,6a,7,8,9-hexahydro-1-oxo-6H-pyrrolo-[1',2':4,5][1,4]oxazino[3,2-h]quinoline-2-carboxylic acid, m.p. >275° C. (dec.), MS: 344 (M+, 58%), 300 (100), 271 (12), 245 (8), 216 (17), 189 (4), 158 (4), 41 (24).

Workup

  1. customthe solvent was evaporated
  2. filtrationfiltered
  3. customCrystallization from ethanol

Sources & evidence

ORD record
ord-728b2a020afa48449ba07025d9e44c7b
Source dataset
uspto-grants-1989_02
Patent number
US04806541

Reaction notes

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