HuagongsheHuagongshe Chemistry Print Report · For research reference only
Protocatechuic Acid → (2S)-2-[(3,4-dihydroxybenzoyl)amino]-N-[2-(3,4-dihydroxyphenyl)ethyl]-N'-trityl-butanediamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Protocatechuic Acid | HCID 72 | — |
| Reactant | N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ngamma-trityl-L-asparagyl]dopamine | HCID 22976130 | — |
| Product | (2S)-2-[(3,4-dihydroxybenzoyl)amino]-N-[2-(3,4-dihydroxyphenyl)ethyl]-N'-trityl-butanediamide | HCID 504775 | — |
Reaction Steps
The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nγ-trityl-L-asparagyl]dopamine (1.3 g, 1.7 mmol, example 7, step A) as described for example 7 (step B) using 3,4-dihydroxybenzoic acid (402 mg, 2.6 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using a solvent gradient from 30% to 60% EtOAc/CH2Cl2 containing 1% AcOH. The title compound was obtained as white crystals (579 mg, 52%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06528655B1 |
| Source dataset | uspto-grants-2003_03 |
| ORD ID | ord-632713bbb1ca4994be14336b02018e90 |
| Source note | uspto-grants-2003_03 |