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Dimethyl Sulfide → Epothilone A
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dimethyl Sulfide | HCID 1068 | — |
| 反応物 | Methyl trifluoromethyl ketone | HCID 9871 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | Potassium bisulfate | HCID 516920 | — |
| 反応物 | Epothilone C | HCID 9891226 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 溶媒 | EDTA disodium salt | HCID 8759 | — |
| 生成物 | Epothilone A | HCID 448799 | 57% |
反応手順
To solution of epothilone C (100 mg, 0.21 mmol) in CH3CN (2.5 mL) and 0.0004 M Na2EDTA (1.5 ml) at 0° C. were added excess CF3COCH3 (1 mL) followed by 2 KHSO5.KHSO4.K2SO4 (potassium peroxymonosulfate) (325 mg, 0.53 mmol) and NaHCO3 (75 mg, 0.89 mmol). The reaction mixture was stirred for 35 min then treated with dimethylsulfide (0.50 mL) and water (3.75 mL). The reaction mixture was warmed to room temperature, extracted with EtOAc (4×10 mL), dried over MgSO4, filtered, and concentrated. The residue was chromatographed with 55% EtOAc/hexanes to give epothilone A (59 mg, 57%) and compound A (30 mg, 29%) as a white solid. m/z: 494(M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06800653B2 |
| 出典データセット | uspto-grants-2004_10 |
| ORD ID | ord-0a21c547423249eeab153057c21af7e4 |
| 出典メモ | uspto-grants-2004_10 |