Hydroxyamine hydrochloride → HCID 136388571, compound

HRID 966404Notes

Reaction equation

HRID 966404 reaction equation
[C:1]([C:4]1[C:14]([OH:15])=[CH:13][C:12]2[CH:11]3[CH2:16][CH:7]([CH2:8][N:9]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:10]3)[C:6]=2[CH:5]=1)(=O)[CH3:2].Cl.[NH2:24][OH:25].CC([O-])=O.[Na+]>CO.O>[F:20][C:18]([F:21])([F:19])[C:17]([N:9]1[CH2:10][CH:11]2[CH2:16][CH:7]([C:6]3[CH:5]=[C:4]([C:1](=[N:24][OH:25])[CH3:2])[C:14]([OH:15])=[CH:13][C:12]=32)[CH2:8]1)=[O:22]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 218647091-(4-Acetyl-5-hydroxy-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 136388571HCID 136388571, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

1-(4-Acetyl-5-hydroxy-10-aza-tricyclo[6.3.1.02.7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (190 mg, 0.605 mmol), hydroxylamine HCl (99 mg, 1.21 mmol) and NaOAc (118 mg, 1.21 mmol) were combined in MeOH (4 mL) and H2O (1 mL) and warmed to 65° C. for 18 hours. The mixture was cooled, diluted with H2O and extracted with EtOAc which was dried (Na2SO4), filtered and concentrated to provide a yellow oil (177 mg, 93%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc which
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d07645b6acc64ee589e9b2f45fc3762e
Source dataset
uspto-grants-2005_10
Patent number
US06951938B2

Reaction notes

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