HuagongsheHuagongshe Chemistry Print Report · For research reference only
Caffeic Acid → (2S)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-N'-trityl-butanediamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Caffeic Acid | HCID 689043 | — |
| Reactant | N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ngamma-trityl-L-asparagyl]dopamine | HCID 22976130 | — |
| Product | (2S)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-N'-trityl-butanediamide | HCID 6478497 | — |
Reaction Steps
N-[Nα-(9-fluorenylmethoxycarbonyl)-Nγ-trityl-L-asparagyl]dopamine (1.0 g, 1.5 mmol) was deprotected according to the indications of general procedure G. The intermediate was coupled with caffeic acid (348 mg, 2.2 mmol) following general procedure D. The crude material was purified by flash chromatography using a solvent gradient from 30% to 70% EtOAc/CHCl3 containing 1% AcOH. The final product was obtained as yellow powder (400 mg, 44%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06528655B1 |
| Source dataset | uspto-grants-2003_03 |
| ORD ID | ord-90e94520d71246bfa99f7a91fecf4f63 |
| Source note | uspto-grants-2003_03 |