HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylcarbodiimide → N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 2-Bromoisonicotinic acid | HCID 222701 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | ethyl (2S)-2-amino-3-(3,4-dimethoxyphenyl)propanoate | HCID 10060820 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester | HCID 53678990 | 64.9% |
Reaction Steps
To methylene chloride (120 ml) are added 3-(3,4-dimethoxyphenyl)alanine ethyl ester (12.4 g), 2-bromoisonicotinic acid (10.9 g), 1-hydroxybenzotriazole monohydrate (8.23 g) and 1,3-dicyclohexylcarbodiimide (11.1 g), and the mixture is stirred at room temperature overnight. The insoluble materials are removed by filtration, and the filtrate is concentrated. The residue is purified by silica gel chromatography (solvent; chloroform:acetone=10:1) to give N-(2-bromoisonicotinoyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester (13.9 g) as an oily product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05965730 |
| Source dataset | uspto-grants-1999_10 |
| ORD ID | ord-5fb5678feb824c4c871dd44cada223c3 |
| Source note | uspto-grants-1999_10 |