HuagongsheHuagongshe Chemistry Print Report · For research reference only
Gallic Acid → N-[(1S)-1-(tert-butoxymethyl)-2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxo-ethyl]-3,4,5-trihydroxy-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Gallic Acid | HCID 370 | — |
| Reactant | N-[Nalpha-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine | HCID 22976135 | — |
| Product | N-[(1S)-1-(tert-butoxymethyl)-2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxo-ethyl]-3,4,5-trihydroxy-benzamide | HCID 504808 | — |
Reaction Steps
The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine (1.16 g, 2.24 mmol, example 42, step A) as described for example 42 (step B) using gallic acid (571 mg, 3.36 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using successively 30%, 40% and 70% EtOAc/CH2Cl2/1% AcOH as the eluent. The title compound was obtained as a white powder (300 mg, 30%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06528655B1 |
| Source dataset | uspto-grants-2003_03 |
| ORD ID | ord-80ae7aeb7de9401a8db9e0b1e4472a9c |
| Source note | uspto-grants-2003_03 |