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 86756959 | HCID 86756959 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86756958 | HCID 86756958 | 35.3% |
Reaction Steps
A solution of 0.429 g of 2-(1-imidazoyl)acetic acid hydrogen bromide and 0.467 g of 2(R)-[4-Cyclohexyl-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]butyl]-2′-isobutyl-4-methylvalerohydrazide in 5 ml of dimethylformamide was treated with 0.230 g of N-ethylmorpholine and 0.422 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and the mixture stirred overnight at room temperature. Evaporation gave a residue which was dissolved in ethyl acetate and washed with water and saturated aqueous sodium chloride solution then dried over anhydrous magnesium sulfate and evaporated. Purification by flash column chromatography on silica gel using methanol/dichloromethane (5:95) as the eluant gave 0.213 g of 2(R)-[4-cyclohexyl-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]butyl]-2′-isobutyl-4-methyl-2′-[2-(1-imidazoyl)acetyl]valerohydrazide in the form of a white foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06239151B1 |
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| Source dataset | uspto-grants-2001_05 |
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| ORD ID | ord-490685493fec452db459b37cad874457 |
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| Source note | uspto-grants-2001_05 |
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