Methanol → HCID 68451235, compound

HRID 2355140Notes

Reaction equation

HRID 2355140 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:44]=[CH:43][CH:42]=[CH:41][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][CH2:26][C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[CH:29][C:28]=2[C:37]([O:39]C)=[O:38])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].CO.O>C1COCC1>[CH2:1]([C:5]1[O:6][C:7]2[CH:44]=[CH:43][CH:42]=[CH:41][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][CH2:26][C:27]2[CH:36]=[CH:35][C:30]([C:31]([OH:33])=[O:32])=[CH:29][C:28]=2[C:37]([OH:39])=[O:38])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 68454868HCID 68454868, compound

Product 1

HCID 68451235HCID 68451235, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of dimethyl 4-[({6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)methyl]isophthalate (155.1 mg, 0.263 mmol), prepared in the previous step, and 1 N NaOH (1.55 mL, 1.55 mmol) in 100 mL of THF, plus 100 mL of methanol, plus 10 mL of water was refluxed under nitrogen for 24 h. By LC/MS starting material remained. An additional 1.55 mL (1.55 mmol) of 1 N NaOH was added and the reaction refluxed for an additional 24 h. After cooling to room temperature the reaction was filtered and then acidified by the addition of 4 mL of 1 N HCl. The reaction was concentrated under reduced pressure to remove most of the THF and methanol. The solid present was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (122.7 mg, 83%) as a white solid, mp 285-287° C. Elemental Analysis for C34H27NO7. 0.11 H2O Calc'd: C, 72.46; H, 4.87; N, 2.49. Found: C, 71.71; H, 4.92; N, 2.35.

Workup

  1. temperaturewas refluxed under nitrogen for 24 h
  2. temperaturethe reaction refluxed for an additional 24 h
  3. filtrationwas filtered
  4. additionacidified by the addition of 4 mL of 1 N HCl
  5. concentrationThe reaction was concentrated under reduced pressure
  6. customto remove most of the THF and methanol
  7. filtrationThe solid present was collected by filtration
  8. washrinsed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-6edf06d8cb5d409f850cf08084fee24f
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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