Hydroxyamine hydrochloride → HCID 86652085, compound

HRID 1510447Notes

Reaction equation

HRID 1510447 reaction equation
[Cl:1][C:2]1[C:3]([C:17]([NH:19][C@@H:20]2[CH2:24][CH2:23][C:22](=O)[CH2:21]2)=[O:18])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.Cl.[NH2:27][OH:28].C(=O)(O)[O-].[Na+]>C(O)C.C(O)C.ClCCl>[Cl:1][C:2]1[C:3]([C:17]([NH:19][C@@H:20]2[CH2:24][CH2:23][C:22](=[N:27][OH:28])[CH2:21]2)=[O:18])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:16])[F:15])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 25182163HCID 25182163, compound

Product 1

HCID 86652085HCID 86652085, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

A suspension of (R)-4-chloro-N-(3-oxocyclopentyl)-5-(4-(trifluoromethyl)phenyl) isoxazole-3-carboxamide (20 mg, 0.054 mmol), hydroxylamine hydrochloride (5 mg, 0.064 mmol), and sodium bicarbonate (7 mg, 0.083 mmol) in ethanol (2 mL) was heated to reflux overnight. The reaction mixture was diluted with ethanol/dichloromethane, filtered through a cotton plug and evaporated in vacuo. Purification by silica gel chromatography, eluting with 8% methanol in dichloromethane gave the title compound as a mixture of cis and trans isomers (10.5 mg, 0.027 mmol). MS (ESI) m/z (M+H+): 388.2/390.3

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationfiltered through a cotton plug
  4. customevaporated in vacuo
  5. customPurification by silica gel chromatography
  6. washeluting with 8% methanol in dichloromethane

Sources & evidence

ORD record
ord-94185ad1a90f43a197fc913c4514a0df
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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