Hydroxyamine hydrochloride → (3-Chloro-4-isoxazol-5-yl-phenyl)-carbamic Acid Tert-butyl Ester

HRID 1249870Notes

Reaction equation

HRID 1249870 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:20])[CH:15]=[CH:16][N:17](C)C)=[C:10]([Cl:21])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.NO>O1CCOCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:20][N:17]=[CH:16][CH:15]=2)=[C:10]([Cl:21])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 54077142HCID 54077142, compound

Product 1

HCID 54457472(3-Chloro-4-isoxazol-5-yl-phenyl)-carbamic Acid Tert-butyl Ester

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of [3-chloro-4-(3-dimethylamino-acryloyl)-phenyl]-carbamic acid tert-butyl ester (270 mg) in dioxane (3 ml) is treated with hydroxylamine hydrochloride (122 mg) and the mixture is stirred at room temperature for 10 days. The mixture is diluted with ethyl acetate, washed successively with water, 5% aqueous sodium bicarbonate, saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent is removed by evaporation under reduced pressure and the resulting residue is chromatographed over silica gel (33% ethyl acetate in hexanes is used as the eluant) to provide the desired product as a colorless solid.

Workup

  1. washwashed successively with water, 5% aqueous sodium bicarbonate, saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent is removed by evaporation under reduced pressure
  4. customthe resulting residue is chromatographed over silica gel (33% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7816fe5caa5f423e9a7ac85a4e74d8c6
Source dataset
uspto-grants-2002_01
Patent number
US06335350B1

Reaction notes

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