Sodium Hydroxide → HCID 90412032, compound

HRID 1522002Notes

Reaction equation

HRID 1522002 reaction equation
[C:1]([C:3]1[C:4]([C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[O:41][CH3:42])=[C:5]2[CH:11]=[C:10]([C:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=3)[N:9](S(C3C=CC=CC=3)(=O)=O)[C:6]2=[N:7][CH:8]=1)#[N:2].[OH-].[Na+]>CO.O1CCCC1.O>[C:1]([C:3]1[C:4]([C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[O:41][CH3:42])=[C:5]2[CH:11]=[C:10]([C:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=3)[NH:9][C:6]2=[N:7][CH:8]=1)#[N:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 90413657HCID 90413657, compound

Product 1

HCID 90412032HCID 90412032, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of Example 236D (400 mg, 0.680 mmol) in 5 mL methanol and 5 mL tetrahydrofuran was added 1N aqueous sodium hydroxide (3398 μL, 3.40 mmol) and the mixture was stirred at room temperature overnight and at 70° C. for 1 hour. The mixture was diluted with water, neutralized to pH 5-6 and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (AnaLogix IntelliFlash 280) eluting with 0-3% methanol in dichloromethane to afford the title compound. MS (ESI+) m/z 449 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (AnaLogix IntelliFlash 280)
  7. washeluting with 0-3% methanol in dichloromethane

Sources & evidence

ORD record
ord-0c35155f9ff84c23bbb4a464831869bd
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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