Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 20640756 | HCID 20640756 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 70248552 | HCID 70248552 | 81.6% |
Reaction Steps
To a solution of Nα-[(2R,3R)-2-(3,4-methylenedioxyphenyl)-3-hydroxyheptanoyl]-L-tryptophan (300 mg) in N,N-dimethylformamide (10 ml) were added potassium carbonate (69 mg) and ethyl iodide (155 mg) and the mixture was stirred at ambient temperature for 3 hours. The mixture was diluted with ethyl acetate (20 ml) and the solution was washed with 0.5N hydrochloric acid (20 ml×2), saturated sodium bicarbonate aqueous solution (20 ml×2) and brine (20 ml) successively and the organic layer was dried over magnesium sulfate. The solution was concentrated in vacuo and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give N [(2R,3R)-2-(3,4-methylenedioxyphenyl)-3-hydroxyheptanoyl]-L-tryptophan ethyl ester as an amorphous powder (260 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06207686B1 |
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| Source dataset | uspto-grants-2001_03 |
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| ORD ID | ord-e56256cb1ccf42a9af6ff7a2ba6df99b |
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| Source note | uspto-grants-2001_03 |
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