2,3-Dimethylacrylic acid, (Z)- → Ingenol Mebutate

HRID 1482752노트

반응식

HRID 1482752 반응식
[CH3:1][C@H:2]1[C:18]23[CH:21]=[C:22]([CH3:25])[C@H:23]([OH:24])[C@@:17]2([OH:26])[C@H:16]2[C:11]([CH2:12][O:13]C(C)(C)[O:15]2)=[CH:10][CH:9]([C:19]3=[O:20])[CH:5]2[C:6]([CH3:8])([CH3:7])[CH:4]2[CH2:3]1.[C:29](O)(=[O:34])/[C:30](=[CH:32]\[CH3:33])/[CH3:31]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH3:33]/[CH:32]=[C:30](\[C:29]([O:24][C@@H:23]1[C@@:17]2([OH:26])[C@H:16]([OH:15])[C:11]([CH2:12][OH:13])=[CH:10][C@H:9]3[C@@H:5]4[C:6]([CH3:7])([CH3:8])[C@@H:4]4[CH2:3][C@@H:2]([CH3:1])[C@:18]2([C:19]3=[O:20])[CH:21]=[C:22]1[CH3:25])=[O:34])/[CH3:31]

참가 물질

5

반응물 2

HCID 6439152,3-Dimethylacrylic acid, (Z)-HCID 91827745(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

생성물 1

HCID 6918670Ingenol Mebutate수율 71.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  1. filtrationwas then filtered through a bed of celite
  2. customevaporated
  3. filtrationThe resulting material was filtered in silica gel (ca. 5 g)
  4. customevaporated
  5. customThe residue was purified by means of silica gel gravity column chromatography (5 g, petroleum ether:EtOAc 85:15)

출처 및 근거

ORD 기록
ord-08d3a0aab1fc47198e497ac3199b9d1c
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416083B2

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