Hydroxylamine → HCID 67122777, compound

HRID 530231Notes

Reaction equation

HRID 530231 reaction equation
[O:1]=[C:2]1[C@@H:6]([O:7][C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])[C@H:5]([O:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[C:4](=O)[O:3]1.[NH2:20][OH:21]>C(OCC)(=O)C>[OH:21][N:20]1[C:2](=[O:1])[C@H:6]([O:7][C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])[C@@H:5]([O:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[C:4]1=[O:3]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86600959HCID 86600959, compound

Product 1

HCID 67122777HCID 67122777, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of compound (30) (5.98 g, 22 mmol) in ethyl acetate (50 mL) at 0° C. was added a 50% aqueous solution of hydroxylamine (1.75 g, 26.4 mmol). The resulting mixture was stirred at room temperature for 3 h and washed successively with aqueous citric acid solution and brine, then dried over anhydrous sodium sulfate. After filtration and concentration in vacuo, the residue was suspended in toluene and the reaction mixture heated under reflux for 5 h, with the azeotropically liberated water being collected in a Dean-Stark apparatus. Toluene was removed in vacuo to afford the title compound (28) (6.3 g, quantitative yield). 1H-NMR (400 MHz, CDCl3): δ 1.22 (d, J=6.8 Hz, 12H), 2.69 (hept, J=6.8 Hz, 2H), 5.48 (s, 2H).

Workup

  1. washwashed successively with aqueous citric acid solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter filtration and concentration in vacuo
  4. temperaturethe reaction mixture heated
  5. temperatureunder reflux for 5 h, with the azeotropically liberated water being
  6. customcollected in a Dean-Stark apparatus
  7. customToluene was removed in vacuo

Sources & evidence

ORD record
ord-e9e0d9da4fc54947b004180c5c634809
Source dataset
uspto-grants-2016_05
Patent number
US09353057B2

Reaction notes

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