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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2369477Generated: October 26, 2026

4-Hydroxyphenylglycine → 2-Amino-2-(3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)acetic acid

https://huagongshe.com/reaction/2369477

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-HydroxyphenylglycineHCID 92143—
Reactant3-(3-(Diisopropylamino)-1-phenylpropyl)-4-hydroxybenzaldehydeHCID 18357317—
ReactantN,N-diisopropyl-3-phenylprop-2-en-1-amineHCID 67084639—
Product2-Amino-2-(3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)acetic acidHCID 53380833—

Reaction Steps

In a preferred embodiment of the invention, 3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxybenzaldehyde (PHB) is synthesized comprising a reaction of 2-amino-2-(4-hydroxyphenyl)acetic acid (hydroxyphenylglycine) with N,N-diisopropyl-3-phenylprop-2-en-1-amine (DIPCA) in the presence of an acid, preferably at 80-150° C., to give 2-amino-2-(3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)acetic acid (HFG), and a further reaction with a suitable oxidant, preferably in water at 30-105° C., to give PHB. Intermediate compound HFG can be isolated. But advantageously and preferably, the synthesis from DIPCA to PHB can be carried out in one pot, without intermediate isolation of HFG.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08703996B2
Source datasetuspto-grants-2014_04
ORD IDord-d6b114f50b5145f7bc527a579e8410e0
Source noteuspto-grants-2014_04