Hydrochloric Acid → HCID 23147059, compound

HRID 495310Notes

Reaction equation

HRID 495310 reaction equation
C(=O)([O-])[O-].[K+].[K+].BrCCOC1CCCCO1.[CH2:17]([O:24][C:25]1[C:26]([CH2:56][CH3:57])=[C:27]([CH2:40][C:41]2[O:45][C:44](=[O:46])[N:43]([CH2:47][CH2:48][O:49]C3CCCCO3)[N:42]=2)[C:28]([Br:39])=[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>CO.CN(C)C=O>[CH2:17]([O:24][C:25]1[C:26]([CH2:56][CH3:57])=[C:27]([CH2:40][C:41]2[O:45][C:44](=[O:46])[N:43]([CH2:47][CH2:48][OH:49])[N:42]=2)[C:28]([Br:39])=[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:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 23147166HCID 23147166, compound

Product 1

HCID 23147059HCID 23147059, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

In the same manner as in the step 1 in Example 317, a crude product of 5-[3,5-bis(benzyloxy)-6-bromo-2-ethylphenylmethyl]-3-(2-tetrahydropyran-2-yloxyethyl)-3H-1,3,4-oxadiazol-2-one was obtained from 5-[3,5-bis(benzyloxy)-6-bromo-2-ethylphenylmethyl]-3H-1,3,4-oxadiazol-2-one (1.1 g, 2.1 mmol) obtained in the above, using potassium carbonate (740 mg, 5.4 mmol), 2-(2-bromoethoxy)tetrahydro-2H-pyran (0.49 mL, 3.2 mmol) and N,N-dimethylformamide (15 mL). Thus obtained, 5-[3,5-bis(benzyloxy)-6-bromo-2-ethylphenylmethyl]-3-(2-tetrahydropyran-2-yloxyethyl)-3H-1,3,4-oxadiazol-2-one was dissolved in methanol (30 mL), then treated with methanol solution (10 mL) of 10% hydrogen chloride, and the reaction solution was concentrated under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate/hexane=1/1) to obtain 5-[3,5-bis(benzyloxy)-6-bromo-2-ethylphenylmethyl]-3-(2-hydroxyethyl)-3H-1,3,4-oxadiazol-2-one (0.85 g, 75%).

Workup

  1. customobtained in the above,
  2. customThus obtained
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-21ef45d53fb749d0a6a5cab82f950757
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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