Hydrochloric Acid → HCID 11510676, compound

HRID 2355131Notes

Reaction equation

HRID 2355131 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([O:23][CH:24]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:25]([O:27]C)=[O:26])[CH:17]=[CH:16]3)=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CO.O>[CH2:1]([C:8]1[O:9][C:10]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([O:23][CH:24]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:25]([OH:27])=[O:26])[CH:17]=[CH:16]3)=[CH:11][N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68452190HCID 68452190, compound

Product 1

HCID 11510676HCID 11510676, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-{[6-(2-benzyl-1,3-oxazol-5-yl)-2-naphthyl]oxy}-3-phenylpropanoate (578 mg, 1.25 mmol), prepared in the previous step, and 1 N NaOH (1.87 mL, 1.87 mmol) in 20 mL of THF, 20 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 2.0 mL of 1N HCl and then concentrated under reduced pressure to remove the THF and the methanol. The white solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (144 mg, 26%) as a white solid, mp 78-82° C. Elemental Analysis for C29H23NO4+0.50 H2O Calc'd: C, 75.97; H, 5.28; N, 3.05. Found: C, 75.29; H, 5.02; N, 2.91.

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-b37c369bb971405090c1f579e3777a2b
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

Loading…