HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(1-Tert-butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid → 3-[4-[5-Cyano-2-(2-hydroxyethylamino)phenylcarbamoylmethoxy]phenoxy]pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(1-Tert-butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid | HCID 18536343 | — |
| Reactant | 3-Amino4-(2-hydroxyethylamino)benzonitrile | HCID 18536434 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | 3-[4-[5-Cyano-2-(2-hydroxyethylamino)phenylcarbamoylmethoxy]phenoxy]pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 69697419 | 75.6% |
Reaction Steps
To a solution of 3-amino-4-(2-hydroxyethylamino)benzonitrile (1.21 g) and 4-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid (2.30 g) in chloroform (50 ml) was added 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroxyquinoline (2.19 g), and the mixture was stirred at room temperature for 15 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4) to give the title compound (2.56 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06562828B1 |
| Source dataset | uspto-grants-2003_05 |
| ORD ID | ord-479ec4dad8e14a0ba282c76192ca851c |
| Source note | uspto-grants-2003_05 |