Ethyl bromoacetate → 1-[3-(Ethoxycarbonylmethoxy)benzoyl]-2-(4,5-diphenyl-2-oxazolyl)piperidine

HRID 380158Notes

Reaction equation

HRID 380158 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[C:13]1[O:14][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)=[O:6].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:38]([O:37][C:35]([CH2:34][O:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[C:13]1[O:14][C:15]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)=[O:6])=[O:36])[CH3:39]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 183673151-(3-Hydroxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidine

Product 1

HCID 183672441-[3-(Ethoxycarbonylmethoxy)benzoyl]-2-(4,5-diphenyl-2-oxazolyl)piperidineYield 74.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(3-hydroxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidine (100 mg), ethyl bromoacetate (61 mg), and K2CO3 (84 mg) in acetonitrile (1.0 ml) was stirred at room temperature overnight and partitioned between water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford 1-[3-(ethoxycarbonylmethoxy)benzoyl]-2-(4,5-diphenyl-2-oxazolyl)piperidine (90 mg) as a colorless oil.

Workup

  1. custompartitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-98cdd177944b46f199d7dd05b25326ef
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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