Hydrochloric Acid → HCID 11721062, compound

HRID 2355119Notes

Reaction equation

HRID 2355119 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][CH:33]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[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>[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][CH:33]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:34]([OH:36])=[O:35])[CH:26]=[CH:25]4)=[CH:20][N:21]=2)=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68454806HCID 68454806, compound

Product 1

HCID 11721062HCID 11721062, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-({6-[2-(1-benzyl-1H-indol-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)-3-phenylpropanoate (117 mg 0.202 mmol), prepared in the previous step, and 1 N NaOH (400 μL, 0.4 mmol) in 20 mL of THF was stirred at room temperature for 16 hr (overnight). The reaction was acidified by the addition of 500 μL 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 (102 mg, 90%) as a dark yellow solid, mp 125-127° C. Elemental Analysis for C37H28N2O4+0.17 mole of H2O Calc'd: C, 78.28; H, 5.03; N, 4.93. Found: C, 76.56; H, 5.59; N, 4.37.

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-56016a8dabd1485bac7af3d1f0047aa2
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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