Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylmorpholine | HCID 7525 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 69953295 | HCID 69953295 | — |
| Reactant | (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide | HCID 86756879 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86756915 | HCID 86756915 | 65% |
Reaction Steps
A solution of 0.309 g of 2-(1-pyrrolidinyl)acetic acid hydrogen bromide in 20 ml of dimethylformamide was treated in sequence with 0.324 ml of N-ethylmorpholine, 0.212 g of 1-hydroxybenzotriazole and 0.301 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. Stirring was continued at room temperature and for 1 hour then 0.450 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide was added. Stirring was continued overnight at room temperature and then the solvent was evaporated and replaced by ethyl acetate. The ethyl acetate phase was washed with 5% aqueous sodium hydrogen carbonate and brine and then dried over anhydrous magnesium sulphate. Evaporation and trituration of the residue with diethyl ether gave 0.363 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2-[2-(1-pyrrolidinyl)acetyl]valerohydrazide in the form of a white solid.
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-6e7db36cb5aa4021bafc8ca9a5827830 |
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| Source note | uspto-grants-2001_05 |
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