HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Formylbenzoic acid → 3-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-formylbenzoyloxymethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Formylbenzoic acid | HCID 12088 | — |
| Reactant | 3-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)propyl]-indol-1-carboxylic acid iodomethyl ester | HCID 20669923 | — |
| Catalyst | Silver | HCID 23954 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 3-[2-(Benzofuran-2-ylmethoxycarbonylamino)-2-(1-phenyl-ethylcarbamoyl)-propyl]-indole-1-carboxylic acid 4-formylbenzoyloxymethyl ester | HCID 20669917 | 80.4% |
Reaction Steps
Compound 7 (1.7 g, 2.5 mmol) and the silver salt of 4-carboxybenzaldehyde (1.29 g, 5.0 mmol) in dry toluene (50 mL) was refluxed for 30 minutes to give a yellow suspension. The solid was removed by filtration through celite, and the solid cake was washed with toluene. The filtrate was concentrated to give a syrup, which was purified by silica gel column eluting with CHCl3 to give compound 19 as a white foam (1.41 g, 80%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06258800B1 |
| Source dataset | uspto-grants-2001_07 |
| ORD ID | ord-729d1986d0a54499bf598fdba7bd9428 |
| Source note | uspto-grants-2001_07 |