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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1860330Generated: November 1, 2026

Gallic Acid → N-[(1S)-1-(tert-butoxymethyl)-2-[2-(3,4-dihydroxyphenyl)ethylamino]-2-oxo-ethyl]-3,4,5-trihydroxy-benzamide

https://huagongshe.com/reaction/1860330

Reaction equation

Participants

RoleNameHCIDCharge
ReactantGallic AcidHCID 370—
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]-3,4,5-trihydroxy-benzamideHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06528655B1
Source datasetuspto-grants-2003_03
ORD IDord-80ae7aeb7de9401a8db9e0b1e4472a9c
Source noteuspto-grants-2003_03