Hydrochloric Acid → HCID 11561273, compound

HRID 2355117Notes

Reaction equation

HRID 2355117 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:34]=[CH:33][CH:32]=[CH:31][C:8]=2[C:9]=1[C:10]1[O:11][C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([O:25][CH2:26][C:27]([O:29]C)=[O:28])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>C1COCC1.O>[CH2:1]([C:5]1[O:6][C:7]2[CH:34]=[CH:33][CH:32]=[CH:31][C:8]=2[C:9]=1[C:10]1[O:11][C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([O:25][CH2:26][C:27]([OH:29])=[O:28])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86603518HCID 86603518, compound

Product 1

HCID 11561273HCID 11561273, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl ({6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetate (295 mg, 0.647 mmol), prepared in the previous step, and 1N NaOH (1.3 mL, 1.3 mmol) in 35 mL of THF and 20 mL of H2O was stirred under nitrogen at room temperature for 14 h (overnight). The reaction was acidified by the addition of 1.4 mL of 1N HCl and then concentrated under reduced pressure to remove the THF. The yellow solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (237 mg, 93%) as a yellow solid, mp 214-216° C. Elemental Analysis for C27H23NO5 Calc'd: C, 73.46; H, 5.25; N, 3.17. Found: C, 73.00; H, 5.49; N, 3.02.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the THF
  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-6c749725ee704c2ea3cec3542e75fcd3
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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