Sodium Hydroxide → HCID 86715584, compound

HRID 928722Notes

Reaction equation

HRID 928722 reaction equation
[N:1]1([C:6]2[CH:22]=[CH:21][C:9]([CH2:10][CH:11]3[C:16](=[O:17])[O:15]C(C)(C)[O:13][C:12]3=[O:20])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[OH-].[Na+]>O>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][CH:11]([C:12]([OH:20])=[O:13])[C:16]([OH:17])=[O:15])=[CH:21][CH:22]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86715583HCID 86715583, compound

Product 1

HCID 86715584HCID 86715584, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(4-(1H-pyrazol-1-yl)benzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (41.4 g, 137 mmol, Intermediate 6: step a) and 3 M aqueous NaOH solution (300 mL, 900 mmol) was heated for 48 hours at 110° C. The mixture was cooled to room temperature, diluted with water (200 mL) and extracted with EtOAc (1×100 mL) and then acidified to pH 1 with concentrated aqueous HCl at 0° C. The resulting mixture was stirred at 0° C. for 1.5 hours, filtered and the filter cake was washed with water. The solids were collected and dried under vacuum at 40° C. to provide the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc (1×100 mL)
  2. customacidified to pH 1 with concentrated aqueous HCl at 0° C
  3. filtrationfiltered
  4. washthe filter cake was washed with water
  5. customThe solids were collected
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-2aea395349244b80be9b5601e27f7788
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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