Water → 4-(2-Acetylamino-6-phenoxy-quinolin-3-yl)-4-(tetrahydro-pyran-4-yl)-butyric acid

HRID 252448Notes

Reaction equation

HRID 252448 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([NH:18][C:19](=[O:21])[CH3:20])[C:12]([CH:22]([CH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[CH2:23][CH2:24][CH:25]=C)=[CH:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=O.[K+].S(=O)(O)[O-].[Na+].[OH-:44].[Na+].[OH2:46]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1.C(O)(=O)C>[C:19]([NH:18][C:13]1[C:12]([CH:22]([CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:23][CH2:24][C:25]([OH:46])=[O:44])=[CH:11][C:10]2[C:15](=[CH:16][CH:17]=[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=2)[N:14]=1)(=[O:21])[CH3:20]

Participants

9

Reactant 5

HCID 962WaterHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 67268795N-{6-phenoxy-3-[1-(tetrahydro-pyran-4-yl)-pent-4-enyl]-quinolin-2-yl}-acetamide

Product 1

HCID 672688004-(2-Acetylamino-6-phenoxy-quinolin-3-yl)-4-(tetrahydro-pyran-4-yl)-butyric acid

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

To a stirred solution of the solid isolated in Step E (6.49 g, 15.1 mmol), tetrabutylammonium bromide (0.078 g, 0.24 mmol), acetic acid (16 mL) in a mixture of benzene (140 mL) and water (140 mL) at 0° C., potassium permanganate (8.34 g, 52.8 mmol) was added slowly. The reaction mixture was then stirred at room temperature for two hours. Sodium bisulfite was added portion wise slowly into the reaction mixture until the color disappeared. The reaction mixture was made basic by adding sodium hydroxide solution (1.0 N). The resulting solution was extracted with diethyl ether twice. The aqueous phase was made acidic (pH 2) by adding hydrochloric acid (3 N). The resulting solution was extracted with chloroform three times. The combined chloroform extracts were washed with brine and dried over magnesium sulfate. The solution was filtered and concentrated to yield 4-(2-acetylamino-6-phenoxy-quinolin-3-yl)-4-(tetrahydro-pyran-4-yl)-butyric acid as a yellow solid.

Workup

  1. extractionThe resulting solution was extracted with diethyl ether twice
  2. additionby adding hydrochloric acid (3 N)
  3. extractionThe resulting solution was extracted with chloroform three times
  4. washThe combined chloroform extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4389b4264aa2497e843e4ea244ce086a
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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