Hydroxyamine hydrochloride → Ethyl 5-(2,4-bis(benzyloxy)-5-isopropylphenyl)isoxazole-3-carboxylate

HRID 2097290Notes

Reaction equation

HRID 2097290 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[C:5](O)=[CH:6][C:7]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:11][C:10]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:8])[CH3:2].Cl.[NH2:37]O>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([C:9]2[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:11][C:10]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:8][N:37]=1)=[O:35])[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178473081HCID 178473081, compound

Product 1

HCID 24773451Ethyl 5-(2,4-bis(benzyloxy)-5-isopropylphenyl)isoxazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-2-hydroxy-4-oxo-but-2-enoic acid ethyl ester (1 eq) was dissolved in ethanol with stirring. Hydroxylamine hydrochloride (1.2 eq) was added and the solution was heated to reflux for 4 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was partitioned between brine and dichloromethane. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give 5-(2,4-Bis-benzyloxy-5-isopropyl-phenyl)-isoxazole-3-carboxylic acid ethyl ester as a solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 4 hours under a nitrogen atmosphere
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between brine and dichloromethane
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9bfabd2d7ba044eeae6e1a6b7504e780
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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