Hydrochloric Acid → HCID 11692076, compound

HRID 2355139Notes

Reaction equation

HRID 2355139 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:40]=[CH:39][CH:38]=[CH:37][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][CH:28]=2)[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].O.Cl>C1COCC1.CO>[CH2:1]([C:5]1[O:6][C:7]2[CH:40]=[CH:39][CH:38]=[CH:37][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:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:35][CH:36]=2)[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 68451249HCID 68451249, compound

Product 1

HCID 11692076HCID 11692076, compoundYield 891.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-[({6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)methyl]benzoate (51 mg, 0.0096 mmol), prepared in the previous step, and 1 N NaOH (145 μL, 0.145 mmol) in 10 mL of THF plus 10 mL of methanol, plus 5 mL of water was refluxed under nitrogen. The reaction was monitored by LC/MS. An additional three aliquots of 145 μL of 1 N NaOH were added over approximately three days of reflux. After cooling to room temperature 1 mL of 1 N HCl was added. The solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (44.3 mg, 89%) as a white solid, mp 251-254° C. Elemental Analysis for C33H27NO5. 0.10 H2O Calc'd: C, 76.31; H, 5.28; N, 2.70. Found: C, 72.79; H, 5.11; N, 2.47.

Workup

  1. temperaturewas refluxed under nitrogen
  2. temperatureof reflux
  3. additionwas added
  4. customThe solid that formed
  5. filtrationwas collected by filtration
  6. washrinsed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c5746a30a01a4aceab47154a7f280b84
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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