Sodium Hydroxide → HCID 90412334, compound

HRID 1522030Notes

Reaction equation

HRID 1522030 reaction equation
[F:1][C:2]1[C:3]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[O:38][CH3:39])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:16][CH2:15][CH:14]([C:17]([O:19]CC)=[O:18])[CH2:13][CH:12]=3)[N:8](S(C3C=CC=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[C:3]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[O:38][CH3:39])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90411721HCID 90411721, compound

Product 1

HCID 90412334HCID 90412334, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of Example 279B (1.1 g, 1.991 mmol) in 20 mL dioxane was treated with 6M aqueous sodium hydroxide (4.98 mL, 29.9 mmol) at 80° C. for 1 hour and at 100° C. for 2 hours. The mixture was cooled and most solvent removed in vacuo. The residue was diluted with 15 mL water and the basic layer extracted with ethyl acetate (twice). The organic layer was discarded. The basic aqueous layer was adjusted to ˜pH 7 with 1M hydrochloric acid, and extracted with ethyl acetate (twice) and dichloromethane (twice). The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Trituration with ethyl acetate, filtration and drying in vacuo gave the title compound. 1H NMR (500 MHz, DMSO-d6) δ 1.60-1.78 (m, 1H) 1.95-2.11 (m, 1H) 2.27-2.48 (m, 3H) 3.39-3.52 (m, 1H) 3.53-3.62 (m, 1H) 3.67-3.81 (m, 3H) 6.12 (s, 1H) 6.54 (s, 1H) 7.07-7.44 (m, 3H) 8.17 (d, J=2.14 Hz, 1H) 11.86 (s, 1H). MS (ESI): 385.2 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. custommost solvent removed in vacuo
  3. additionThe residue was diluted with 15 mL water
  4. extractionthe basic layer extracted with ethyl acetate (twice)
  5. extractionextracted with ethyl acetate (twice) and dichloromethane (twice)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. filtrationTrituration with ethyl acetate, filtration
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-856b0421c4e44cc5bae710e5f7037905
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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