Hydroxyamine hydrochloride → HCID 66759309, compound

HRID 880352Notes

Reaction equation

HRID 880352 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1[C:33](=[O:42])[CH2:34][C:35](=O)[C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:44]O>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=2)[C:10]=1[C:33]1[O:42][N:44]=[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66758581Ethyl 4-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-2,4-dioxobutanoate

Product 1

HCID 66759309HCID 66759309, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of ethyl 4-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-2,4-dioxobutanoate (5 g, 9 mmol) and hydroxylamine hydrochloride (0.74 g, 15 mmol, 1.2 eq) in ethanol (mL 50) was refluxed for 2 hours. The solution was concentrated to a small volume and diluted with ethyl acetate. After washing with brine and drying, the solvent was removed and the residue was carefully chromatographed on silica gel eluting with hexane/ethyl acetate 6/1, to provide the title compound (4.1 g, 82% yield).

Workup

  1. concentrationThe solution was concentrated to a small volume
  2. additiondiluted with ethyl acetate
  3. washAfter washing with brine
  4. customdrying
  5. customthe solvent was removed
  6. customthe residue was carefully chromatographed on silica gel eluting with hexane/ethyl acetate 6/1

Sources & evidence

ORD record
ord-5c6648198cf546548555f30d815e969c
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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