Hydrochloric Acid → HCID 23147524, compound

HRID 495308Notes

Reaction equation

HRID 495308 reaction equation
C(=O)([O-])[O-].[K+].[K+].BrCCOC1CCCCO1.[CH2:17]([O:24][C:25]1[C:26]([CH2:61][CH3:62])=[C:27]([CH2:45][C:46]2[O:50][C:49](=[O:51])[N:48]([CH2:52][CH2:53][O:54]C3CCCCO3)[N:47]=2)[C:28]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:30]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.C(=O)([O-])O.[Na+]>CO.CN(C)C=O>[CH2:17]([O:24][C:25]1[C:26]([CH2:61][CH3:62])=[C:27]([CH2:45][C:46]2[O:50][C:49](=[O:51])[N:48]([CH2:52][CH2:53][OH:54])[N:47]=2)[C:28]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:30]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 516892Sodium BicarbonateHCID 23147607HCID 23147607, compound

Product 1

HCID 23147524HCID 23147524, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

In the same manner as in the step 1 in Example 317, 5-{[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]methyl}-3-(2-tetrahydropyran-2-yloxyethyl)-3H-1,3,4-oxadiazol-2-one was obtained from 5-{[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]methyl}-3H-1,3,4-oxadiazol-2-one (280 mg, 0.57 mmol) obtained in the step 2 in Example 315, using potassium carbonate (200 ng, 1.4 mmol), 2-(2-bromoethoxy)tetrahydro-2H-pyran (0.13 mL, 0.86 mmol) and N,N-dimethylformamide (3.0 mL). The resulting 5-{[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]methyl}-3-(2-tetrahydropyran-2-yloxyethyl)-3H-1,3,4-oxadiazol-2-one was dissolved in methanol (3.0 mL), and methanol solution (2.0 mL) of 10% hydrogen chloride was added thereto and stirred at room temperature for 30 minutes. The reaction solution was neutralized with aqueous saturated sodium hydrogencarbonate solution added thereto, and then extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate/hexane=1/1 to 1/0) to obtain 5-{[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]methyl}-3-(2-hydroxyethyl)-3H-1,3,4-oxadiazol-2-one (260 mg, 85%).

Workup

  1. customobtained in the step 2 in Example 315
  2. additionadded
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate/hexane=1/1 to 1/0)

Sources & evidence

ORD record
ord-dc10de7821cc426b8f860b0ced7a306f
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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