Water → HCID 54747342, compound

HRID 553540Notes

Reaction equation

HRID 553540 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:23]=[C:22]3[C:17]([C:18]([OH:33])=[C:19]([C:26](=[O:32])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])[C:20](=[O:25])[N:21]3[CH3:24])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=[O:7])(C)(C)C.OC1C2C(=CC(C3C=CC(C(OC(C)(C)C)=O)=CC=3)=CC=2)N(C)C(=O)C=1C(=O)CCC=O.OOS([O-])=O.[K+].O>CN(C=O)C>[C:29]([CH2:28][CH2:27][C:26]([C:19]1[C:20](=[O:25])[N:21]([CH3:24])[C:22]2[C:17]([C:18]=1[OH:33])=[CH:16][CH:15]=[C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:13][CH:12]=1)[CH:23]=2)=[O:32])([OH:31])=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 67407862HCID 67407862, compoundHCID 86631268HCID 86631268, compound

Product 1

HCID 54747342HCID 54747342, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(7-(4-(tert-Butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-4-oxobutanoic acid. tert-Butyl 4-(4-hydroxy-1-methyl-2-oxo-3-(4-oxobutanoyl)-1,2-dihydroquinolin-7-yl)benzoate (130 mg, 299 μmol) was dissolved in DMF (1493 μl). Oxone (184 mg, 299 μmol) was added to the mixture at room temperature, and the resulting mixture was stirred for 1 hour. Water was added to precipitate the product from solution. The mixture was filtered, washed with water and ether, and dried in a vacuum oven to give the title compound as an off-white solid.

Workup

  1. customto precipitate the product from solution
  2. filtrationThe mixture was filtered
  3. washwashed with water and ether
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-228cd640d6ac479e8b36b48feaac7fe1
Source dataset
uspto-grants-2011_11
Patent number
US08048894B2

Reaction notes

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