Hydrochloric Acid → HCID 11682723, compound

HRID 2355128Notes

Reaction equation

HRID 2355128 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[O:12][C:13]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[CH:22]=[C:21]([O:26][CH2:27][C:28]([O:30]C)=[O:29])[CH:20]=[CH:19]4)=[CH:14][N:15]=2)=[CH:3]1.[OH-].[Na+].Cl>C1COCC1.CO.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[O:12][C:13]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[CH:22]=[C:21]([O:26][CH2:27][C:28]([OH:30])=[O:29])[CH:20]=[CH:19]4)=[CH:14][N:15]=2)=[CH:3]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86603521HCID 86603521, compound

Product 1

HCID 11682723HCID 11682723, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl ({6-[2-(1-methyl-1H-indol-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetate (254 mg, 0.925 mmol), prepared in the previous step, and 1N NaOH (925 μL, 0.925 mmol) in 30 mL of THF, 30 mL of methanol and 10 mL of H2O was stirred at room temperature for 16 h (overnight). The reaction was acidified by the addition of 1.0 mL of 1N HCl and then concentrated under reduced pressure to remove the THF and methanol. The yellow solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (218 mg, 89%) as a yellow solid, mp 269-272° C. Elemental Analysis for C24H18N2O4 Calc'd: C, 72.35; H, 4.55; N, 7.03. Found: C, 71.97; H, 4.78; N, 6.73.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the THF and methanol
  3. customThe yellow solid that formed
  4. filtrationwas collected by filtration
  5. washrinsed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-fb8289e734654e33a3f106545b811db2
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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