Hydroxyamine hydrochloride → 1,1-Dimethylethyl 4-(hydroxyimino)-4-phenylbutylcarbamate

HRID 352111Notes

Reaction equation

HRID 352111 reaction equation
O=[C:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].Cl.[NH2:21][OH:22].O.O.O.C([O-])(=O)C.[Na+]>C(O)C>[OH:22][N:21]=[C:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 14267858tert-Butyl (4-oxo-4-phenylbutyl)carbamateHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 739931561,1-Dimethylethyl 4-(hydroxyimino)-4-phenylbutylcarbamateYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,1-dimethylethyl 4-oxo-4-phenylbutylcarbamate (2.4 g, 9.1 mmol), hydroxylamine hydrochloride (1.27 g, 2 equiv.) and sodium acetate trihydrate (2.5 g, 2 equiv.) was stirred and heated under reflux in 20% aqueous ethanol (60 ml) for 7 h. The reaction mixture was then concentrated and the residue partitioned between saturated aqueous sodium bicarbonate (100 ml) and ethyl acetate (200 ml). The organic extract was dried over magnesium sulphate and concentrated to afford a colourless solid (2.4 g, 95%).

Workup

  1. temperatureheated
  2. concentrationThe reaction mixture was then concentrated
  3. customthe residue partitioned between saturated aqueous sodium bicarbonate (100 ml) and ethyl acetate (200 ml)
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-259c42bac06247e89b27511ca0be64a9
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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