Sodium Hydroxide → HCID 58893385, compound

HRID 871088Notes

Reaction equation

HRID 871088 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)=[CH:10][C:3]=12.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)=[CH:10][C:3]=12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90408880HCID 90408880, compound

Product 1

HCID 58893385HCID 58893385, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 14A (6.500 g, 13.32 mmol) and 20% sodium hydroxide (6 mL) in dioxane (80 mL) was heated at 90° C. for 7 hours. The mixture was concentrated and the residue was treated with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The precipitate was filtered, washed with ethyl acetate/ether and dried under vacuum to give of the title compound. The filtrate was concentrated and purified by flash chromatography on silica (ISCO Companion), eluting with a gradient of 3:7 to 2:8 heptanes/ethyl acetate to give an additional quantity of the title compound. MS (ESI+) m/z 333.9 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationThe precipitate was filtered
  8. washwashed with ethyl acetate/ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-811c3b682ae949839a02aaa8a5b5f348
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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