Trifluoroacetic anhydride → Anhydrodihydroartemisnin

HRID 1610787

반응식

HRID 1610787 반응식
[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

참가 물질

5

반응물 2

HCID 9845Trifluoroacetic anhydrideHCID 456410Npc182939

생성물 1

HCID 393517Anhydrodihydroartemisnin수율 36.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To absolution 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), 2.00-2.05 (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-1 S); m/z (EI) 380 (M+); Anal. Calc. for C15H22O4: C, 67.67; H, 8.27; Found: C, 67.63; H, 8.51.

후처리

  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)

출처 및 근거

ORD 기록
ord-17252ff2f1c24da783fcddc09c3b411e
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06984640B1

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