Propanal → 7-Ethyl-10-Hydroxycamptothecin

HRID 129525

반응식

HRID 129525 반응식
[CH3:1][CH2:2][C@@:3]1([OH:27])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16]([CH:17]=[C:18]([OH:26])[CH:19]=[CH:20]2)=[CH:15][C:14]=1[CH2:13]3)=[O:11].[CH:28](=O)[CH2:29]C.S(=O)(=O)(O)O.FC(F)(F)C(O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[CH3:28][CH2:29][C:15]1[C:14]2[CH2:13][N:12]3[C:10](=[O:11])[C:5]4[CH2:6][O:7][C:8]([C@:3]([OH:27])([CH2:2][CH3:1])[C:4]=4[CH:25]=[C:24]3[C:23]=2[N:22]=[C:21]2[C:16]=1[CH:17]=[C:18]([OH:26])[CH:19]=[CH:20]2)=[O:9]

참가 물질

8

반응물 5

HCID 527PropanalHCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 24412Potassium PersulfateHCID 97226Hydroxycamptothecin

생성물 1

HCID 1048427-Ethyl-10-Hydroxycamptothecin

시약·촉매·용매 2

HCID 62662Ferrous sulfate heptahydrate촉매HCID 962Water용매2회

실험 절차

The 10-hydroxy camptothecin (800 mg; 2.2 mmol) is suspended in water (24 ml). Iron (II) sulfate heptahydrate (250 mg, 0.85 millimoles) is added to the suspension and then followed by the addition of propionaldehyde (3 ml). The reaction mixture is then cooled in an ice bath and concentrated sulfuric acid (1 ml) and trifluoroacetic acid (24 ml) are added. After stirring the homogeneous solution for 15 minutes, potassium persulfate (3.5 g; 6 mol equivalent) is added, and the mixture is slowly warmed to room temperature. After approximately 15 hours, the reaction mixture is diluted with water and the product is extracted using excess chloroform. The crude product is washed thrice with 5% methanol in ether and dried to obtain 806 mg of the desired compound. 1H NMR (300 MHz; DMSO-d6): 0.87 δ (3H, t, J=7 Hz); 1.62 δ (3H, t, J=7 Hz); 1.85 δ (2H, 1q, J=5 Hz); 3.18 δ (2H, q, J=5 Hz); 5.19 δ (2H, m); 5.40 δ (2H, s); 6.51 δ (1H, bs); 7.23 δ (2H, m); 7.39 δ (1H, d, J=10 Hz); 8.01 δ (1H, d, J=9Hz) 13C NMR: δ7.3, 13.6, 22.4, 29.8, 72.0, 95.8, 102.7, 117.9, 120.4, 124.8, 144.6, 145.3, 156.5, 158.3, 200.1 FAB MS: 403 (M+1)+

후처리

  1. temperatureThe reaction mixture is then cooled in an ice bath
  2. waitAfter approximately 15 hours
  3. extractionthe product is extracted
  4. washThe crude product is washed thrice with 5% methanol in ether
  5. customdried

출처 및 근거

ORD 기록
ord-90c9690576e740ad9fcb27059b249382
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468754

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