Potassium Phosphate, Tribasic → HCID 69374561, compound

HRID 1353103Notes

Reaction equation

HRID 1353103 reaction equation
Cl[C:2]1[C:24]([N+:25]([O-:27])=[O:26])=[C:23]([Cl:28])[C:22]([F:29])=[CH:21][C:3]=1[C:4]([C:6](=[CH:12][NH:13][C@@H:14]([CH3:20])[CH2:15][O:16][C:17](=[O:19])[CH3:18])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C>[C:17]([O:16][CH2:15][C@@H:14]([N:13]1[C:2]2[C:3](=[CH:21][C:22]([F:29])=[C:23]([Cl:28])[C:24]=2[N+:25]([O-:27])=[O:26])[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12]1)[CH3:20])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 178472049HCID 178472049, compound

Product 1

HCID 69374561HCID 69374561, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

45.69 g of (+) ethyl 2-(2,4-dichloro-3-nitro-5-fluorobenzoyl)-3-[(1-acetoxyprop-2(S)-yl)amino]acrylate was dissolved in 270 ml of acetonitrile under heating to 70˜75° C. 32.25 g (1.5 eq.) of K3PO4 was added in portions to the reaction mixture, which was then stirred at the same temperature for 4 hours. The reaction mixture was filtered under a reduced pressure and washed with 500 ml of dichloromethane. The filtrate was concentrated under a reduced pressure. The resulting residue was dissolved in 300 ml of dichloromethane and then washed with water. The organic layer was concentrated under a reduced pressure to give 46.2 g of (−) ethyl N-(acetoxy-prop-2(S)-yl)-6-fluoro-7-chloro-8-nitro-4-quinolone-3-carboxylate (Yield: 95.4%).

Workup

  1. temperatureunder heating to 70˜75° C
  2. filtrationThe reaction mixture was filtered under a reduced pressure
  3. washwashed with 500 ml of dichloromethane
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. dissolutionThe resulting residue was dissolved in 300 ml of dichloromethane
  6. washwashed with water
  7. concentrationThe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-0ff26cb7ae094ca196d0d054e22a1227
Source dataset
uspto-grants-2007_05
Patent number
US07220861B2

Reaction notes

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