Sulfuric Acid → 5-(1-Hydroxy-1-methylethyl)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623816Notes

Reaction equation

HRID 1623816 reaction equation
C[Mg]Br.[C:4]([C:7]1[CH:8]=[CH:9][C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:11]([CH:21]=1)[C:12]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:13])(=[O:6])[CH3:5].OS(O)(=O)=O.[C:35]([O-])(O)=O.[Na+]>O1CCCC1.C(OCC)(=O)C>[OH:6][C:4]([C:7]1[CH:8]=[CH:9][C:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:11]([CH:21]=1)[C:12]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:13])([CH3:35])[CH3:5]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 671072525-Acetyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamideHCID 178418573HCID 178418573, compound2×

Product 1

HCID 699368045-(1-Hydroxy-1-methylethyl)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3M Methylmagnesium bromide (0.10 ml, 0.29 mmol) was added to a solution of 5-acetyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 72; 100 mg, 0.29 mmol) in tetrahydrofuran (3 ml) at 0° C. The solution was stirred for 45 minutes. Another 3 equivalents of 3M methylmagnesium bromide (300 ul) were added at 0° C. and solution was stirred for 18 hours. 1N H2SO4 (5 ml) was then added, the mixture was stirred for 3 minutes, then ethyl acetate (10 ml) was added. The acid layer was basified to pH 9 using saturated NaHCO3 solution. The organic layer was washed with saturated NaHCO3 solution (5 ml), dried (MgSO4) and the solvent was removed in vacuo. The residue was purified by MDAP to give the title compound as a white solid. 61 mg.

Workup

  1. stirringsolution was stirred for 18 hours
  2. stirringthe mixture was stirred for 3 minutes
  3. washThe organic layer was washed with saturated NaHCO3 solution (5 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-a013831f884843aeb5d8ac894ce01e12
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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