Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylmorpholine | HCID 7525 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 69952674 | HCID 69952674 | — |
| Reactant | HCID 69953393 | HCID 69953393 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69950498 | HCID 69950498 | 37.6% |
Reaction Steps
A solution of 0.510 g of 2(R)-[4-cyclopentyl-1(S)-(tert-butoxycarbonyl)-butyl]-2′-isobutyl-4-methylvalerohydrazide in 10 ml of dimethylformamide was treated in sequence with 0.308 g of 2-(1-imidazoyl)acetic acid hydrogen bromide, 0.172 g of N-ethylmorpholine and 0.286 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride and then stirred overnight at room temperature. The mixture was diluted with diethyl ether and washed with water and saturated aqueous sodium chloride solution. Drying over anhydrous magnesium sulphate and evaporation gave a residue which was purified by column chromatography on silica gel, using ethyl acetate/hexane (1:3) and then dichloromethane/methanol (3:1) for the elution, to give 0.255 g of 2(R)-[4-cyclopentyl-1(S)-(tert-butoxycarbonyl)-butyl]-2′-isobutyl-2′-[2-(1-imidazoyl)acetyl]-4-methylvalerohydrazide in the form of a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06239151B1 |
|---|
| Source dataset | uspto-grants-2001_05 |
|---|
| ORD ID | ord-598bee38b4bb46d092bec7b64c750f05 |
|---|
| Source note | uspto-grants-2001_05 |
|---|