Trifluoroacetic anhydride → Anhydrodihydroartemisnin

HRID 271547

反応式

HRID 271547 の反応式
[CH3:1][C@H:2]1[C@@H:11]2[CH2:12][CH2:13][C:14]3([CH3:18])[O:16][O:17][C@:10]42[C@H:5]([C@@H:6]([CH3:20])[C@@H:7](O)[O:8][C@@H:9]4[O:15]3)[CH2:4][CH2:3]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][C@H:2]1[C@@H:11]2[CH2:12][CH2:13][C@@:14]3([CH3:18])[O:16][O:17][C@:10]42[C@H:5]([C:6]([CH3:20])=[CH:7][O:8][C@@H:9]4[O:15]3)[CH2:4][CH2:3]1

参加物

5

反応物 2

HCID 9845Trifluoroacetic anhydrideHCID 456410Npc182939

生成物 1

HCID 393517Anhydrodihydroartemisnin収率 36.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of dihydroartemisinin (500 mg, 1.86 mmol) in dichloromethane (28 ml) at 0° C. under nitrogen was added 4-(N,N-dimethylamino)pyridine (37 mg) and trifluoroacetic anhydride (0.79 ml, 5.58 mmol). The mixture was allowed to warm to room temperature and stirred overnight. The solution was then concentrated in vacuo. The residue was purified by flash chromatography (SiO2; ether:hexane from 0.5:9.5 to 1.5:8.5) to give 9,10-anhydro-10-deoxoartemisinin (9,10-anhydroartemisinin) (180 mg, 25%) as a white solid. M.p. 100° C.; [α]D20.5+155.74° (c.0.0101 in CHCl3); νmax (film): 2948, 2922, 2862, 2850, 1684, 1432, 1372, 1334, 1198, 1178, 1158, 1142, 1114, 1078, 1028, 1016, 992, 954, 944, 904, 880, 828, 812; δH: 6.18 (1H, s, H-10), 5.54 (1H, s, H-12), 2.40 (1H, ddd, J=17.1, 13.2, 4.14 Hz, H-9), 2.00-2.09 (2H, m), 1.88-1.95 (1H, m), 1.07-1.73 (8H, m), 1.58 (3H, d, J=1.37 Hz, H-16), 1.42 (3H, s, H-14), 0.98 (3H, d, J=5.98 Hz, H-15); m/z (EI): 380 (M+); Anal. Calc. for C15H22O4: C, 67.67; H, 8.27; Found: C, 67.63; H, 8.51

後処理

  1. concentrationThe solution was then concentrated in vacuo
  2. customThe residue was purified by flash chromatography (SiO2; ether:hexane from 0.5:9.5 to 1.5:8.5)

出典と根拠

ORDレコード
ord-ecd3c3e79a51495e9b6b5df1f0e7e318
出典データセット
uspto-grants-2008_11
特許番号
US07452915B2

関連ノート

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