Water → HCID 10392180, compound

HRID 1708551Notes

Reaction equation

HRID 1708551 reaction equation
C(Cl)Cl.[F:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:16])[C:14]=1[F:15])[N:11]([NH:17][CH3:18])[CH:10]=[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]2=[O:24].[C:25]([O:29][C:30]([C:32](=[CH2:40])[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:31])([CH3:28])([CH3:27])[CH3:26].O>C(OCC)(=O)C.[Ti](Cl)(Cl)(Cl)Cl>[F:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:16])[C:14]=1[F:15])[N:11]([N:17]([CH3:18])[CH2:40][CH:32]([C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:10]=[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]2=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 11096368Propanedioic acid, methylene-, bis(1,1-dimethylethyl) esterHCID 11098599Ethyl 6,7,8-trifluoro-1-(methylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 10392180HCID 10392180, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methylene chloride (10 ml) solution of ethyl 6,7,8-trifluoro-1-methylamino-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.0 g) and tert-butyl 2-tert-butoxycarbonylacrylate (1.52 g) was cooled in an ice bath in nitrogen atmosphere, and titanium tetrachloride (632.4 mg) was dropwise added thereto. After 30 minutes, this was diluted with ethyl acetate (100 ml) and then with water (100 ml). The organic layer was separated out, washed with water (2×50 ml), dried over magnesium sulfate and concentrated under reduced pressure to obtain an yellow syrup product. The syrup product was subjected to column chromatography with silica gel and eluted with a mixed solvent of methylene chloride/ethyl acetate (10/1) to obtain ethyl 6,7,8-trifluoro-1-[N-methyl-N-{2,2-bis(tert-butoxycarbonyl)ethyl}amino]-1,4-dihydro-4-oxoquinoline-3-carboxylate (988 mg), as a white solid.

Workup

  1. additionwas dropwise added
  2. customThe organic layer was separated out
  3. washwashed with water (2×50 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain an yellow syrup product
  7. washeluted with a mixed solvent of methylene chloride/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-2a9a0b77e8084c59bf48c3d434d1bd46
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

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