HuagongsheHuagongshe Chemistry Print Report · For research reference only
Caffeic Acid → N-[(1S)-1-(tert-butoxymethyl)-2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxo-ethyl]-3,4-bis[(4-fluorophenyl)methoxy]benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Caffeic Acid | HCID 689043 | — |
| Reactant | 3,4-Di-(4-fluorobenzyloxy)benzoic acid | HCID 18627055 | — |
| 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-bis[(4-fluorophenyl)methoxy]benzamide | HCID 504861 | — |
Reaction Steps
The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamine (610 mg, 1.2 mmol, example 42, step A) as described for example 42 (step B) using 3,4-di-(4-fluorobenzyloxy)benzoic acid (653 mg, 1.8 mmol, step A of this example) instead of caffeic acid. The crude material was purified by flash chromatography using successively 15%, 35% and 50% EtOAc/CH2Cl2 as the eluent. The title compound was obtained as a yellow powder (207 mg, 27%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06528655B1 |
| Source dataset | uspto-grants-2003_03 |
| ORD ID | ord-4720430f4c6e4fdea395d172c47c2bcf |
| Source note | uspto-grants-2003_03 |