Water → HCID 86669899, compound

HRID 1506414Notes

Reaction equation

HRID 1506414 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[C:24]4[CH2:23][CH2:22][C:21]5[N:20]=[C:19]([CH:25]([OH:28])CO)[CH:18]=[CH:17][C:16]=5[C:15]=4[O:14][N:13]=3)[C:8]=2[C:29]([F:32])([F:31])[F:30])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([O-])(=O)(=O)=O.[Na+].O>C1COCC1.C(OCC)(=O)C>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[C:24]4[CH2:23][CH2:22][C:21]5[N:20]=[C:19]([CH:25]=[O:28])[CH:18]=[CH:17][C:16]=5[C:15]=4[O:14][N:13]=3)[C:8]=2[C:29]([F:31])([F:32])[F:30])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 67169953HCID 67169953, compound

Product 1

HCID 86669899HCID 86669899, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydroisoxazolo[5,4-f]quinolin-7-yl)ethane-1,2-diol (Preparation 54G, 0.030 g, 0.068 mmol) in THF (1 mL) at room temperature was added sodium periodate (0.022 g, 0.101 mmol) followed by water (0.05 mL). The reaction mixture was stirred at room temperature for 2.5 h. The reaction mixture was diluted with ethyl acetate (30 mL), washed with water (10 mL), and brine (10 mL). The combined aqueous layers were extracted with ethyl acetate (30 mL), dried over and anhydrous sodium sulfate and concentrated to give 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydroisoxazolo[5,4-f]quinoline-7-carbaldehyde (0.029 g, 0.071 mmol, quantitative yield) as a tan solid. The compound had an HPLC ret. time=3.08 min. (condition A); LC/MS M+1=412.1.

Workup

  1. washwashed with water (10 mL), and brine (10 mL)
  2. extractionThe combined aqueous layers were extracted with ethyl acetate (30 mL)
  3. dry with materialdried over and anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a159370a83014cfba815832f115aab96
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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