Hydrochloric Acid → HCID 11634262, compound

HRID 2355120Notes

Reaction equation

HRID 2355120 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[CH:28]=[C:27]([O:32][CH2:33][C:34]([O:36]C)=[O:35])[CH:26]=[CH:25]4)=[CH:20][N:21]=2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[CH:28]=[C:27]([O:32][CH2:33][C:34]([OH:36])=[O:35])[CH:26]=[CH:25]4)=[CH:20][N:21]=2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86603519HCID 86603519, compound

Product 1

HCID 11634262HCID 11634262, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl ({6-[2-(1-benzyl-1H-indol-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetate (271 mg, 0.555 mmol), prepared in the previous step, and 1N NaOH (1.11 mL, 1.11 mmol) in 35 mL of THF plus 20 mL of H2O was stirred at room temperature for 15 h (overnight). The reaction was acidified by the addition of 1.2 mL of 1N HCl and then concentrated under reduced pressure to remove the THF. The white solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (236 mg, 90%) as a white solid, mp 238-242° C. Elemental Analysis for C30H22N2O4+0.32 mole of H2O. Calc'd: C, 75.03; H, 4.75; N, 5.83. Found: C, 74.67; H, 5.34; N, 5.19.

Workup

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

Sources & evidence

ORD record
ord-943e955867774d28977042072eb535ee
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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