Sodium Hydroxide → HCID 15986633, compound

HRID 730071Notes

Reaction equation

HRID 730071 reaction equation
C(=[N:14][C:15]1[C:28]2[O:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20](=[C:29]3[CH2:35][CH:34]4[N:36](C(=O)C(F)(F)F)[CH:31]([CH2:32][CH2:33]4)[CH2:30]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO.[OH-].[Na+]>CO.O.C(Cl)Cl>[CH:31]12[NH:36][CH:34]([CH2:33][CH2:32]1)[CH2:35][C:29](=[C:20]1[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([NH2:14])[C:28]=3[O:27][C:26]3[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:30]2

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 57833605HCID 57833605, compound

Product 1

HCID 15986633HCID 15986633, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-{3-[4-(benzhydrylidene-amino)-xanthen-9-ylidene]-8-aza-bicyclo[3.2.1]oct-8-yl}-2,2,2-trifluoroethanone in methanol (0.1 to 1 M solution) may be treated with sodium acetate (2 to 4 equiv) and hydroxylamine hydrochloride (1 to 3 equiv) and stirred at rt for 1 to 4 days. Sodium hydroxide may be added to make the solution basic, and the solution may be stirred at rt for 1 to 5 hr. Methylene chloride and water may be added, and the organic layer may be separated. After drying over a suitable drying agent such as potassium carbonate, filtration, and evaporation, the residue may be purified via reverse phase column chromatography to yield Compound 2c.

Workup

  1. stirringthe solution may be stirred at rt for 1 to 5 hr
  2. customthe organic layer may be separated
  3. dry with materialAfter drying over a suitable drying agent such as potassium carbonate, filtration, and evaporation
  4. customthe residue may be purified via reverse phase column chromatography

Sources & evidence

ORD record
ord-25abc55c8cdf409ab1762c323dfcd4af
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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