Hydrochloric Acid → HCID 11612836, compound

HRID 2355126Notes

Reaction equation

HRID 2355126 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][CH:27]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[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][CH:27]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[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 68452478HCID 68452478, compound

Product 1

HCID 11612836HCID 11612836, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-({6-[2-(1-methyl-1H-indol-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)-3-phenylpropanoate (185 mg, 0.369 mmol), prepared in the previous step, and 1 N NaOH (550 μL, 0.55 mmol) in 10 mL of THF, 10 mL of methanol and 5 mL of H2O was stirred at room temperature for 18 h (overnight). The reaction was acidified by the addition of 600μL 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 (102 mg, 90%) as a white solid, mp 149-151° C. Elemental Analysis for C31H24N2O4+0.36 H2O Calc'd: C, 75.22; H, 5.03; N, 5.66. Found: C, 75.28 ;H, 5.22; N, 5.39.

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-7b7f8e4595204b38aeb563effd59ab7c
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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