HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Hydroxyphenylglycine → 2-Amino-2-(3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Hydroxyphenylglycine | HCID 92143 | — |
| Reactant | 3-(3-(Diisopropylamino)-1-phenylpropyl)-4-hydroxybenzaldehyde | HCID 18357317 | — |
| Reactant | N,N-diisopropyl-3-phenylprop-2-en-1-amine | HCID 67084639 | — |
| Product | 2-Amino-2-(3-(3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)acetic acid | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08703996B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-d6b114f50b5145f7bc527a579e8410e0 |
| Source note | uspto-grants-2014_04 |