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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1860344Generated: October 26, 2026

Caffeic Acid → N-[(1S)-1-(tert-butoxymethyl)-2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxo-ethyl]-3,4-bis[(4-fluorophenyl)methoxy]benzamide

https://huagongshe.com/reaction/1860344

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCaffeic AcidHCID 689043—
Reactant3,4-Di-(4-fluorobenzyloxy)benzoic acidHCID 18627055—
ReactantN-[Nalpha-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-seryl]dopamineHCID 22976135—
ProductN-[(1S)-1-(tert-butoxymethyl)-2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxo-ethyl]-3,4-bis[(4-fluorophenyl)methoxy]benzamideHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06528655B1
Source datasetuspto-grants-2003_03
ORD IDord-4720430f4c6e4fdea395d172c47c2bcf
Source noteuspto-grants-2003_03