Water → tert-butyl N-(4-methyl-1-oxopentan-2-yl)carbamate

HRID 2401256Notes

Reaction equation

HRID 2401256 reaction equation
[OH:1][CH2:2][CH:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH:5]([CH3:7])[CH3:6].I(C1C=CC=CC=1C(O)=O)(=O)=O.O>CS(C)=O>[CH3:6][CH:5]([CH3:7])[CH2:4][CH:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 1087942-Iodoxybenzoic acidHCID 546110tert-butyl N-(1-hydroxy-4-methylpentan-2-yl)carbamate

Product 1

HCID 546109tert-butyl N-(4-methyl-1-oxopentan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of tert-butyl (1-hydroxy-4-methylpentan-2-yl)carbamate (2.7 g) in DMSO (60 mL) was added 2-iodoxybenzoic acid (3.5 g), and the mixture was stirred at room temperature for 3 hr. Water was added thereto, the resulting insoluble matter was filtered off, and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. After the dessicant was filtered off, the filtrate was concentrated under reduced pressure to afford a crude product of tert-butyl (4-methyl-1-oxopentan-2-yl)carbamate.

Workup

  1. filtrationthe resulting insoluble matter was filtered off
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter the dessicant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1068b36a8d4649d2b34630d4b93a9902
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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