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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2S,5R)-5-Allyl-1-((S)-2-methylamino-pent-4-enoyl)-pyrrolidine-2-carboxylic acid phenethyl-amide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| 反応物 | N-Allylglycine | HCID 76651 | — |
| 反応物 | (2s,5r)-5-Allyl-pyrrolidine-2-carboxylic acid phenethyl-amide | HCID 57612770 | — |
| 反応物 | Homoallylproline amide | HCID 131729076 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | (2S,5R)-5-Allyl-1-((S)-2-methylamino-pent-4-enoyl)-pyrrolidine-2-carboxylic acid phenethyl-amide | HCID 66995156 | — |
反応手順
AllylGlyOH (10.5 g, 26.4 mmol) is suspended in dichloromethane (200 mL) and EDCI (5.1 g, 26.4 mmol) and DMAP (3.2 g, 26.4 mmol) are added to obtain a clear solution. 11E homoallylproline amide in dichloromethane (50 mL) is added and stirred overnight. The product is quenched with saturated bicarb and extracted with dichloromethane, followed by washing with brine, drying over anhydrous magnesium sulfate, filtering and concentrating. The crude is used in following deprotection. LCMS characterization ES+456.1 (m+1).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07989441B2 |
| 出典データセット | uspto-grants-2011_08 |
| ORD ID | ord-d706b5114cdb4706bd870839d835e45f |
| 出典メモ | uspto-grants-2011_08 |