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(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane → 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane | HCID 9861019 | — |
| 反応物 | N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide | HCID 19031947 | — |
| 溶媒 | Ethanol | HCID 702 | — |
| 生成物 | 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide | HCID 57286140 | 92.7% |
反応手順
A solution of 2.98 g of 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane and 2.1 g of N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide in 50 ml of ethanol was heated at reflux for 10 hours and the solvent was then removed by evaporation. Chromatography on silica gel using System H for the elution then gave 4.7 g of 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide as a mixture of four diastereomers: MS: m/e 508 [M+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05620987 |
| 出典データセット | uspto-grants-1997_04 |
| ORD ID | ord-7ff4e79b9bb74f40af70585bb8a7bf69 |
| 出典メモ | uspto-grants-1997_04 |