Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylmorpholine | HCID 7525 | — |
| Reactant | Isobutylhydrazine | HCID 542420 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 20658017 | HCID 20658017 | — |
| Reactant | HCID 178526939 | HCID 178526939 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 69951698 | HCID 69951698 | 82.5% |
Reaction Steps
A solution of 0.78 g of 2(R)-[3-benzamido-1(S)-(tert-butoxycarbonyl)propyl]-4-methylvaleric acid in 10 ml of dichloromethane was cooled to 0° C. under nitrogen and treated sequentially with 0.80 ml of N-ethylmorpholine, 0.437 g of hydroxybenzotriazole hydrate, and 0.50 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. The mixture was stirred for 5 minutes at 0° C. and then 1.1 g of isobutyl hydrazine was added. Stirring was continued overnight at room temperature and then the solvent was evaporated. The residue was dissolved in ethyl acetate and washed with 5% aqueous sodium hydrogen carbonate, water, 2M aqueous hydrogen chloride, and saturated aqueous sodium chloride. Drying over anhydrous magnesium sulfate, filtration and evaporation of the solvent gave 0.763 g of 2(R)-[3-benzamido-1(S)-(tert-butoxycarbonyl)propyl]-2′-isobutyl-4-methylvalerohydrazide in the form of an off-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-32d2f0e0f28448e2ae5355ed0be9eb44 |
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| Source note | uspto-grants-2001_05 |
|---|