Water → HCID 57855827, compound

HRID 475562Notes

Reaction equation

HRID 475562 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10]2[O:11][CH:12]=[C:13]([CH2:15][NH:16][C:17](=[O:27])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][CH3:26])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].N12CCCN=[C:34]1[CH2:33][CH2:32][CH2:31]CC2.BrCC1CC1.O>C(O)C>[CH:33]1([CH2:34][O:1][C:2]2[CH:3]=[C:4]([C:10]3[O:11][CH:12]=[C:13]([CH2:15][NH:16][C:17](=[O:27])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[O:24][CH2:25][CH3:26])[N:14]=3)[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])[CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81503BromomethylcyclopropaneHCID 68981450HCID 68981450, compound

Product 1

HCID 57855827HCID 57855827, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.2 g quantity of the N-[2-(3-hydroxy-4-methoxy phenyl)oxazol-4-ylmethyl]-2-ethoxybenzamide obtained in Example 2 and 0.3 ml of 1,8-diazabicyclo[5,4,0]undec-7-ene were dissolved in 4 ml of ethanol, and 0.14 g of (bromomethyl)cyclopropane was added thereto. The mixture was heated and refluxed overnight. The reaction mixture was allowed to cool, water was then added thereto, and extraction was performed with ethyl acetate. After washing with water twice, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to give 0.18 g of white powdery N-[2-(3-cyclopropylmethoxy-4-methoxyphenyl)oxazol-4-ylmethyl]-2-ethoxybenzamide.

Workup

  1. temperatureThe mixture was heated
  2. temperaturerefluxed overnight
  3. temperatureto cool
  4. extractionextraction
  5. washAfter washing with water twice
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-358f9f07ef494dd2ab8701b8b79f3afe
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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