Ethyl Acetate → HCID 68431453, compound

HRID 2092065Notes

Reaction equation

HRID 2092065 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH:9]([CH3:15])[C:10]([O:12]CC)=[O:11])[N:5]=[CH:4][C:3]=1[NH:16][C@@H:17]1[CH2:22][C@@H:21]2[CH2:23][C@@H:19]([C:20]2([CH3:25])[CH3:24])[C@H:18]1[CH3:26].[OH-].[Na+].C(OCC)(=O)C>O1CCOCC1>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH:9]([CH3:15])[C:10]([OH:12])=[O:11])[N:5]=[CH:4][C:3]=1[NH:16][C@@H:17]1[CH2:22][C@@H:21]2[CH2:23][C@@H:19]([C:20]2([CH3:24])[CH3:25])[C@H:18]1[CH3:26]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 68431536HCID 68431536, compound

Product 1

HCID 68431453HCID 68431453, compoundYield 158.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-{5-bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}propanoate (149 mg, 0.349 mmol) in 1,4-dioxane (1 mL) was stirred with 1 M aqueous sodium hydroxide (0.698 mL, 0.698 mmol) at room temperature for 5.5 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 1 M hydrochloric acid and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give the desired product (220 mg, quant.).

Workup

  1. additionwas added
  2. washthe organic layer was washed with 1 M hydrochloric acid and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1848f53423664b17964f9cf3ff6049c7
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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