関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Thiophenol | HCID 7969 | — |
| 反応物 | Tributylphosphine | HCID 13831 | — |
| 反応物 | diazenedicarboxylic acid bis(N,N-piperidide) | HCID 5702657 | — |
| 反応物 | Methyl (R)-3-[(benzyloxycarbonyl)amino]-4-hydroxybutanoate | HCID 59108917 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | (R)-methyl 3-(benzyloxycarbonylamino)-4-(phenylthio)butanoate | HCID 66723634 | 70.4% |
反応手順
To a solution of benzenethiol (11.16 ml, 108.65 mmol), (R)-methyl 3-(benzyloxycarbonylamino)-4-hydroxybutanoate (INTERMEDIATE 4, 26.4 g, 98.77 mmol) and tributylphosphine (34.5 ml, 138.28 mmol) in anhydrous THF (350 ml) under nitrogen atmosphere was added. A solution of (E)-diazene-1,2-diylbis(piperidin-1-ylmethanone) (34.9 g, 138.22 mmol) in anhydrous THF (350 ml) was added dropwise over a 30 minute period. During the addition a white precipitate was formed and stirring was continued for 2 hours after the addition was complete. The white precipitate was filtered off and evaporation of the volatiles under reduced pressure gave a residue, which was purified by column chromatography (ISCO, eluting with 0→100% EtOAc/hexanes) to give the title product (25.0 g, yield: 70%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09248140B2 |
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| 出典データセット | uspto-grants-2016_02 |
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| ORD ID | ord-70854a4df8004817a9dbb8969b39e22f |
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| 出典メモ | uspto-grants-2016_02 |
|---|
