Water → HCID 67268164, compound

HRID 252455Notes

Reaction equation

HRID 252455 reaction equation
[NH2:1][C:2]1[C:11]([C@H:12]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:13][CH2:14][CH2:15][OH:16])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:8]=2)[N:3]=1.CC(C)=[O:32].OS(O)(=O)=O.O=[Cr](=O)=O.OS(O)(=O)=O.O>CC(C)=O>[NH2:1][C:2]1[C:11]([C@H:12]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:13][CH2:14][C:15]([OH:32])=[O:16])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 67268348HCID 67268348, compoundHCID 131709961Jones' reagent

Product 1

HCID 67268164HCID 67268164, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To an ice cold solution of 4-(2-amino-6-phenoxy-quinoline-3-yl)-4-(S)-cyclohexyl-butan-1-ol (0.44 g, 1.12 mmol) in acetone (15 mL) was added Jones reagent (0.7 M solution in a 0.12:1 mixture of concentrated H2SO4:H2O, 16.0 mL, 11.3 mmol) dropwise, and the reaction mixture was stirred for 3.0 h. The excess reagent was quenched by adding isopropyl alcohol, and the resulting slurry was filtered through Celite®. The crude material obtained by removal of the solvent was purified by silica gel column chromatography using 30% MeOH in CHCl3 to yield 4-(2-amino-6-phenoxy-quinoline-3-yl)-4-(S)-cyclohexyl-butyric acid.

Workup

  1. customThe excess reagent was quenched
  2. additionby adding isopropyl alcohol
  3. filtrationthe resulting slurry was filtered through Celite®
  4. customThe crude material obtained by removal of the solvent
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9bc43511632d4132bf9467b5f450b631
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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