Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
2,3-Dimethylacrylic acid, (Z)- → Ingenol Mebutate
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | 2,3-Dimethylacrylic acid, (Z)- | HCID 643915 | — |
| 반응물 | (4S,5R,6R,18R)-4,5-dihydroxy-3,8,8,15,15,18-hexamethyl-7,9-dioxapentacyclo[11.5.1.01,5.06,11.014,16]nonadeca-2,11-dien-19-one | HCID 91827745 | — |
| 촉매 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 용매 | Toluene | HCID 1140 | — |
| 생성물 | Ingenol Mebutate | HCID 6918670 | 71.5% |
반응 단계
A solution of ingenol-5,20-acetonide (100 mg, 0.26 mmol), angelic acid (39 mg, 0.39 mmol, 1.5 mol. equiv.) and DMAP (48 mg, 0.39 mmol, 1.5 mol. equiv.) in toluene (4 ml), was stirred at room temperature for 2 hours and was then filtered through a bed of celite and evaporated. The resulting material was filtered in silica gel (ca. 5 g) and evaporated. The residue was purified by means of silica gel gravity column chromatography (5 g, petroleum ether:EtOAc 85:15) until obtaining over 80 mg of ingenol-3-angelate with a purity>99%. For physical and spectroscopic data, see Hohmann J et al. Planta Medica 2000, 66, 291-294.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US09416083B2 |
| 출처 데이터셋 | uspto-grants-2016_08 |
| ORD ID | ord-08d3a0aab1fc47198e497ac3199b9d1c |
| 출처 메모 | uspto-grants-2016_08 |