Trifluoroacetic acid → (6aR,7S,9aS,11S,13aS)-11-amino-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

HRID 1417617노트

반응식

HRID 1417617 반응식
[NH2:1][C@@H:2]1[C:38]([CH3:40])([CH3:39])[C@H:37]2[C@@:5]3([O:33][C:9]4[C:10]5[CH2:11][N:12](C(OC(C)(C)C)=O)[C:13](=[O:25])[C:14]=5[CH:15]=[C:16]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[C:8]=4[CH2:7][C@:6]3([CH3:42])[C@@H:34]([CH3:41])[CH2:35][CH2:36]2)[CH2:4][CH2:3]1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[NH2:1][C@@H:2]1[C:38]([CH3:40])([CH3:39])[C@H:37]2[C@@:5]3([O:33][C:9]4[C:10]5[CH2:11][NH:12][C:13](=[O:25])[C:14]=5[CH:15]=[C:16]([O:17][CH2:18][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=5)[C:8]=4[CH2:7][C@:6]3([CH3:42])[C@@H:34]([CH3:41])[CH2:35][CH2:36]2)[CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 86753816(6aR,7S,9aS,11S,13aS)-11-amino-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

생성물 1

HCID 86753817(6aR,7S,9aS,11S,13aS)-11-amino-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of Compound (45a) (50 mg, 0.087 mmol) in 5 ml of dry dichloromethane were added 30 μl (0.28 mmol) of anisole and 35 μl (0.45 mmol) of trifluoroacetic acid, and the mixture stirred for 3 hours at room temperature. Under ice-cooling, to the reaction mixture was added an aqueous saturated sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The extract was washed with water and an aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 30 mg (73%) of the crude Compound (46a) as a powdery material.

후처리

  1. temperatureUnder ice-cooling, to the reaction mixture
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialan aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b2f34ff962b04615a97094c1659273e9
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05876984

반응 노트

불러오는 중…