Sulfuric Acid → HCID 21070485, compound

HRID 1371772Notes

Reaction equation

HRID 1371772 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH:22]2[OH:31])[N:3]=1.S(=O)(=O)(O)O.C(O)(C)C.C(=O)(O)[O-].[Na+]>CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O.[O-2].[Cr+6].[O-2].[O-2]>[NH2:1][C:2]1[C:7]([C:8](=[O:9])[C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[CH:6][N:5]=[C:4]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:28])=[O:29])[CH2:23][C:22]2=[O:31])[N:3]=1

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 69013806HCID 69013806, compound

Product 1

HCID 21070485HCID 21070485, compound

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 131709961Jones' reagentSolvent

Procedure

To a stirred solution of alcohol (65 mg, 0.14 mmol, Example 306) in acetone (4 mL), Jones reagent (made by adding 0.5 mL of concentrated sulfuric acid to a solution of chromium(VI) oxide, 0.67 g, Aldrich, in 2 mL of water) was slowly added until the orange color persisted for 20 minutes. The mixture was stirred for 1 hour and 2 mL of isopropanol was added. The mixture was again stirred for 30 minutes followed by slow addition of saturated sodium bicarbonate solution until pH=7. The mixture was extracted with ethyl acetate/tetrahydrofuran (2:1, 3×10 mL) and the extracts were combined and dried with sodium sulfate. The solvent was removed and the residue was chromatographed on HPLC (20–70%) to give a white solid, 4.3 mg, 7%. MS (ES) MH+=456.

Workup

  1. stirringThe mixture was again stirred for 30 minutes
  2. extractionThe mixture was extracted with ethyl acetate/tetrahydrofuran (2:1, 3×10 mL)
  3. dry with materialdried with sodium sulfate
  4. customThe solvent was removed
  5. customthe residue was chromatographed on HPLC (20–70%)
  6. customto give a white solid, 4.3 mg, 7%

Sources & evidence

ORD record
ord-36d4b8452fb54f6a8b0ad66af1d0b7b4
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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