Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Bromoacetamide | HCID 69632 | — |
| Reactant | HCID 86630047 | HCID 86630047 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86630048 | HCID 86630048 | 49.1% |
Reaction Steps
In 5 ml of N,N-dimethylformamide is dissolved 2.0 g of ethyl 3-{5-[(2,4-diisobutoxyphenyl)-(hydroxyimino)methyl]-2-isobutoxyphenyl}propanoate, to which is added 0.19 g of 60% sodium hydride. The mixture thus obtained is stirred at ambient temperature for 30 minutes. Then, 1.07 g of 2-bromoacetamide is added and the mixture thus obtained is stirred at ambient temperature for one hour and further at 80° C. for 15 minutes. The reaction mixture is added to a mixture of ethyl acetate and water, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1) to obtain 1.09 g of ethyl 3-{5-[[(2-amino-2-oxoethoxy)imino](2,4-diisobutoxyphenyl)methyl]-2-isobutoxyphenyl}propanoate as a colorless oily product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07314888B1 |
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| Source dataset | uspto-grants-2008_01 |
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| ORD ID | ord-7b80bb4d89194e05a3990433e2b917b6 |
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| Source note | uspto-grants-2008_01 |
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