Hydrochloric Acid → HCID 11625679, compound

HRID 2355135Notes

Reaction equation

HRID 2355135 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[O:13][C:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([O:27][CH2:28][C:29]([O:31]C)=[O:30])[CH:21]=[CH:20]3)=[CH:15][N:16]=1.[OH-].[Na+].Cl>C1COCC1.CO.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[O:13][C:14]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([O:27][CH2:28][C:29]([OH:31])=[O:30])[CH:21]=[CH:20]3)=[CH:15][N:16]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86603522HCID 86603522, compound

Product 1

HCID 11625679HCID 11625679, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl ({6-[2-(2-naphthylmethyl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetate (184 mg, 0.433 mmol), prepared in the previous step, and 1N NaOH (650 μL, 0.65 mmol) in 10 mL of THF, 10 mL of methanol and 5 mL of H2O was refluxed for 2 h. The reaction was acidified by the addition of 700 μL of 1N HCl and then concentrated under reduced pressure to remove the THF and methanol. The white solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (175 mg, 99%) as a white solid, mp 258-260° C. Elemental Analysis for C26H19NO4+0.20 H2O Calc'd: C, 75.61; H, 4.73; N, 3.39. Found: C, 75.41; H, 4.91; N, 3.22

Workup

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

Sources & evidence

ORD record
ord-01f44f0259ad4847a7146be50836cdbc
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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