HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 4-{(S)-4-tert-butoxycarbonyl-2-[(6-methyl-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | ethyl 4-[(2S)-2-amino-5-tert-butoxy-5-oxopentanoyl]piperazine-1-carboxylate | HCID 66651766 | — |
| Product | 4-{(S)-4-tert-butoxycarbonyl-2-[(6-methyl-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester | HCID 67463479 | — |
Reaction Steps
Intermediate 86.2 (214 mg), HOBT hydrate (168 mg) and EDCI hydrochloride (210 mg) were dissolved in DMF (7 ml). After 15 min stirring, 4-((S)-2-amino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester (377 mg) was added and the stirring was continued overnight at RT. A saturated NH4Cl solution was added and the mixture was extracted with EA. The org. phases were dried (Na2SO4) and evaporated off. Column chromatography (EA/Hept 1/3 to 1/1) of the crude offered the compound still contaminated by some starting material. It was then taken up in EA and washed with a Na2CO3 solution, dried and evaporated off to give 462 mg of the pure desired compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08048881B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-0610ada155494cdbb256f1f17b3f32d4 |
| Source note | uspto-grants-2011_11 |