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Dimethylformamide → Methyl (S)-2-benzyloxycarbonylamino-3-chlorocarbonylpropionate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Oxalyl chloride | HCID 65578 | — |
| 反応物 | Z-Asp-OMe | HCID 7021783 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | Methyl (S)-2-benzyloxycarbonylamino-3-chlorocarbonylpropionate | HCID 11055664 | — |
反応手順
Z-asp-OMe (175 g, 622 mmol) was dissolved in THF (1750 ml) and admixed with 2 ml of DMF. 86.9 g (684 mmol) of oxalyl chloride were dissolved in 200 ml of THF (slightly exothermic), cooled back to room temperature (RT) and added dropwise to the solution of the amino acid over 1 hour (h). After a further hour at RT, the solution was initially sparged with nitrogen for 10 min, concentrated on a rotary evaporator at a maximum of 30° C. and coevaporated repeatedly with toluene. The resulting dirty white solid was dried to constant weight under in-house vacuum (about 1.5 mbar) and reacted further without further purification. Yield: 186.6 g (quantitative).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08039480B2 |
| 出典データセット | uspto-grants-2011_10 |
| ORD ID | ord-360bc2998965435eb2730a0ec78bba49 |
| 出典メモ | uspto-grants-2011_10 |