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

HRID 1482752ノート

反応式

HRID 1482752 の反応式
[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]

参加物

5

反応物 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

生成物 1

HCID 6918670Ingenol Mebutate収率 71.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-08d3a0aab1fc47198e497ac3199b9d1c
出典データセット
uspto-grants-2016_08
特許番号
US09416083B2

反応ノート

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