Sodium Hydroxide → HCID 11635852, compound

HRID 456847Notes

Reaction equation

HRID 456847 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:10]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[CH:29]=[C:28]([O:33][CH2:34][C:35]3[CH:44]=[CH:43][C:38]([C:39]([O:41]C)=[O:40])=[CH:37][C:36]=3[C:45]([O:47]C)=[O:46])[CH:27]=[CH:26]4)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.CO.O>[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:10]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[CH:29]=[C:28]([O:33][CH2:34][C:35]3[CH:44]=[CH:43][C:38]([C:39]([OH:41])=[O:40])=[CH:37][C:36]=3[C:45]([OH:47])=[O:46])[CH:27]=[CH:26]4)=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 18439039HCID 18439039, compound

Product 1

HCID 11635852HCID 11635852, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of dimethyl 4-{[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]methyl}isophthalate (165 mg, 0.254 mmol), prepared in the previous step, and 1 N NaOH (1.52 mL, 1.52 mmol) in 30 mL of THF plus 20 mL of methanol plus 5 mL of water was refluxed under nitrogen for 6 h. The reaction was filtered, cooled to room temperature, acidified by the addition of 5 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF and methanol. The solid present was collected by filtration, rinsed with water and dried under reduced pressure at 60° C. to give the title compound (148 mg, 94%) as a yellow solid, mp 250–252° C. Elemental Analysis for C37H26F3NO5.0.18 C4H8O.0.34 H2O Calc'd: C, 70.71; H, 4.42; N, 2.19. Found: C, 70.65; H, 4.34; N, 2.13.

Workup

  1. temperaturewas refluxed under nitrogen for 6 h
  2. filtrationThe reaction was filtered
  3. additionacidified by the addition of 5 mL of 1 N HCl
  4. concentrationconcentrated under reduced pressure
  5. customto remove the THF and methanol
  6. filtrationThe solid present was collected by filtration
  7. washrinsed with water
  8. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-21ebf04084b94fe49b529ecbe4794063
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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