Hydrochloric Acid → HCID 11678167, compound

HRID 2355115Notes

Reaction equation

HRID 2355115 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:41]=[CH:40][CH:39]=[CH:38][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][CH:26]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[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>[CH2:1]([C:5]1[O:6][C:7]2[CH:41]=[CH:40][CH:39]=[CH:38][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][CH:26]([CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:27]([OH:29])=[O:28])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68454490HCID 68454490, compound

Product 1

HCID 11678167HCID 11678167, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-({6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)-3-phenylpropanoate (346 mg, 0.633 mmol), prepared in the previous step, and 1 N NaOH (1.26 mL, 1.26 mmol) in 50 mL of THF was stirred at room temperature for 18 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 (266 mg, 77%) as a yellow solid, mp 174-177° C. Elemental Analysis for C34H29NO5+0.039 H2O Calc'd: C, 76.72; H, 5.51; N, 2.63. Found: C, 75.36; H, 5.48; N, 2.44.

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-3f4ea2a7dfd54e99af2dd720ce6cf2b2
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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