Methanol → HCID 22747784, compound

HRID 1641594Notes

Reaction equation

HRID 1641594 reaction equation
C([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([NH:20][S:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:16][CH2:15]2)=[O:13])=[CH:7][CH:6]=1)(C)(C)C.[CH:27]1[CH:32]=C(C([O-])=O)C(C(O[O-])=O)=[CH:29][CH:28]=1.[Mg+2].C[OH:42]>C(Cl)Cl.O>[CH2:32]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([NH:20][S:21]([C:23]([CH3:24])([CH3:25])[CH3:26])(=[O:42])=[O:22])[CH2:16][CH2:15]2)=[O:13])=[CH:9][CH:10]=1)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 887MethanolHCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 66739112HCID 66739112, compound

Product 1

HCID 22747784HCID 22747784, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a mixture of 2 ml of methanol and 2 ml of methylene chloride, 291 mg of 4-t-butylsulfinylaminopiperidine-1-carboxylic acid(4-t-butylphenyl)amide was dissolved. To the mixture, 570 mg of 80%-MMPP (magnesium monoperoxyphthalate hexahydrate) was added and the mixture was stirred at room temperature for 2 hours. The solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate anhydride. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography to give 130 mg of 4-t-butylsulfonylaminopiperidine-1-carboxylic acid(4-butylphenyl)amide (I-120).

Workup

  1. dissolutionwas dissolved
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate anhydride
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-35cf59e6d42748dba8317ecb596a1f3b
Source dataset
uspto-grants-2012_02
Patent number
US08115027B2

Reaction notes

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