Acetohydroxamic Acid → HCID 67180081, compound

HRID 2362247Notes

Reaction equation

HRID 2362247 reaction equation
C([NH:4][OH:5])(=O)C.CC(C)([O-])C.[K+].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[CH:23][CH:22]=[C:21]2[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:16][C:15]=1F)#[N:13].C(OCC)(=O)C>CN(C=O)C.[Cl-].[Na+].O>[NH2:13][C:12]1[C:14]2[CH:19]=[CH:18][C:17]([N:20]3[C:24]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)=[CH:23][CH:22]=[C:21]3[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:16][C:15]=2[O:5][N:4]=1

Participants

7

Reactant 4

HCID 1990Acetohydroxamic AcidHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 67179951HCID 67179951, compound

Product 1

HCID 67180081HCID 67180081, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

In 4 mL of dry DMF was dissolved acetohydroxamic acid (57 mg, 0.765 mmol), followed by potassium t-butoxide (86 mg, 0.765 mmol) at ambient temperature. After this mixture had been stirred for 30 min, compound 47-1 (200 mg, 0.510 mmol) was added and stirred overnight. The reaction mixture was poured into a mixture of brine (30 mL) and ethyl acetate (30 mL). The organic phase was separated, the aqueous layer was extracted EA (20 mL×3). The combined organic phase was washed with brine (30 mL), dried over anhydrous Na2SO4, filtered, concentrated and purified by silica gel column chromatography (PE:EA=1:1) to afford 47-2 as a yellow oil (80 mg, 39%).

Workup

  1. stirringstirred overnight
  2. customThe organic phase was separated
  3. extractionthe aqueous layer was extracted EA (20 mL×3)
  4. washThe combined organic phase was washed with brine (30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (PE:EA=1:1)

Sources & evidence

ORD record
ord-bf76b1c4b31544e79ca6ebd9da3b5688
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

Loading…