2-Ethoxybenzoic acid → HCID 68982390, compound

HRID 475560Notes

Reaction equation

HRID 475560 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:17]2[O:18][CH:19]=[C:20]([CH2:22][NH2:23])[N:21]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:46]([O:48][C:49]1[CH:57]=[CH:56][CH:55]=[CH:54][C:50]=1[C:51](O)=[O:52])[CH3:47]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:17]2[O:18][CH:19]=[C:20]([CH2:22][NH:23][C:51](=[O:52])[C:50]3[CH:54]=[CH:55][CH:56]=[CH:57][C:49]=3[O:48][CH2:46][CH3:47])[N:21]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 672522-Ethoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68981656HCID 68981656, compound

Product 1

HCID 68982390HCID 68982390, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 3.5 g quantity of the [2-(3-benzyloxy-4-methoxy phenyl)oxazol-4-yl]methylamine obtained in Reference Example 7 was suspended in 70 ml of acetone. To the obtained suspension were added 2.3 g of 1-hydroxybenzotriazole, 3.3 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 3.8 g of 2-ethoxybenzoic acid, and the mixture was heated and refluxed for one hour. The reaction mixture was cooled, and acetone was distilled off under reduced pressure. Water was added to the residue, and extraction was then performed with ethyl acetate. The organic layer was washed with water twice, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1) to give 4.6 g of white powdery N-[2-(3-benzyloxy-4-methoxyphenyl)oxazol-4-ylmethyl]-2-ethoxybenzamide.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for one hour
  3. temperatureThe reaction mixture was cooled
  4. distillationacetone was distilled off under reduced pressure
  5. additionWater was added to the residue, and extraction
  6. washThe organic layer was washed with water twice
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-16cd6f09bb78468fabb5f5523d7e43d5
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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