Sodium Hydroxide → HCID 11497424, compound

HRID 1820841Notes

Reaction equation

HRID 1820841 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:23][CH:24]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:25]([O:27]C)=[O:26].[OH-].[Na+]>C1COCC1.CO.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:23][CH:24]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:25]([OH:27])=[O:26]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 68982761HCID 68982761, compound

Product 1

HCID 11497424HCID 11497424, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-{[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}-3-phenylpropanoate (197 mg, 0.363 mmol), prepared in the previous step, and 1 N NaOH (544 μL, 0.544 mmol) in 20 mL of THF plus 20 mL of methanol plus 10 mL of water was refluxed under nitrogen for 3 h. The reaction was filtered, acidified by the addition of 2 mL of 1 N HCl and then concentrated under reduced pressure. The solid was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (178 mg, 92%) as a white solid, mp 220-224° C. Elemental Analysis for C28H20BrNO3S+0.18H2O Calc'd: C, 63.02; H, 3.85; N, 2.62. Found: C, 63.13; H, 3.70; N, 2.54.

Workup

  1. temperaturewas refluxed under nitrogen for 3 h
  2. filtrationThe reaction was filtered
  3. additionacidified by the addition of 2 mL of 1 N HCl
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe solid was collected by filtration
  6. washrinsed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-2d46c30b43824be4ad838d49012dc35b
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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