HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2s,5r)-5-Allyl-1-[(s)-2-((s)-2-dimethylamino-propionylamino)-pent-4-enoyl]-pyrrolidine-2-carboxylic acid phenethyl-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | (2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid | HCID 7009590 | — |
| Reactant | (2S,5R)-5-Allyl-1-((S)-2-amino-pent-4-enoyl)-pyrrolidine-2-carboxylic acid phenethyl-amide | HCID 57612851 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2s,5r)-5-Allyl-1-[(s)-2-((s)-2-dimethylamino-propionylamino)-pent-4-enoyl]-pyrrolidine-2-carboxylic acid phenethyl-amide | HCID 66994769 | — |
Reaction Steps
Boc-N-MeAlaOH (5.36 g, 26.4 mmol) is suspended in dichloromethane (200 mL) and EDCI (5.4 g, 28 mmol) and DMAP (3.4 g, 28 mmol) are added to obtain a clear solution. 11G in dichloromethane (50 mL) is added and stirred overnight followed by quenching with saturated bicarb and extracting with dichloromethane then washing with brine, drying over anhydrous magnesium sulfate, filtering and concentrating. LCMS characterization ES+541.2 (m+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07989441B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-6425ddb72f4c4809a4f758072192fe84 |
| Source note | uspto-grants-2011_08 |