Toluene → HCID 58019115, compound

HRID 1967456Notes

Reaction equation

HRID 1967456 reaction equation
[Br:1][C:2]1[C:3]([O:25][CH3:26])=[CH:4][C:5](F)=[C:6]([CH:23]=1)[C:7]([C:9](=[CH:15][NH:16][C@H:17]([CH2:21][OH:22])[CH:18]([CH3:20])[CH3:19])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:23]=[C:6]2[C:5](=[CH:4][C:3]=1[O:25][CH3:26])[N:16]([C@H:17]([CH2:21][OH:22])[CH:18]([CH3:20])[CH3:19])[CH:15]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:7]2=[O:8]

Participants

6

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 178472055HCID 178472055, compound

Product 1

HCID 58019115HCID 58019115, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
45 °C

Procedure

Ethyl 2-(5-Bromo-2-fluoro-4-methoxybenzoyl)-3-((S)-1-hydroxymethyl-2-methylpropylamino)acrylate (19.5 g) was dissolved in DMF (50 mL), and potassium carbonate (8.32 g) was added. After stirring at 45° C. for 8 hr, the completion of the reaction was confirmed by HPLC. Toluene (100 mL) and 5% brine (100 mL) were added to the reaction mixture, and after stirring, the toluene layer was separated. The toluene layer was washed 3 times with 10% brine (100 mL). After washing, toluene was evaporated under reduced pressure. Toluene (50 mL) was added to the concentrate residue, and the mixture was concentrated again under reduced pressure. The obtained crude ethyl 6-bromo-7-methoxy-1-((S)-1-hydroxymethyl-2-methylpropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (17.4 g) was directly used in the next step.

Workup

  1. stirringafter stirring
  2. customthe toluene layer was separated
  3. washThe toluene layer was washed 3 times with 10% brine (100 mL)
  4. washAfter washing
  5. customtoluene was evaporated under reduced pressure
  6. additionToluene (50 mL) was added to the concentrate residue
  7. concentrationthe mixture was concentrated again under reduced pressure

Sources & evidence

ORD record
ord-371788ec827244b9b5a3c3c3cd39b943
Source dataset
uspto-grants-2013_04
Patent number
US08420821B2

Reaction notes

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