Cyclopentylamine → N6-cyclopentyl-5'-O-ethyladenosine

HRID 6669

반응식

HRID 6669 반응식
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:23][C@H:22]([CH2:24][O:25][CH2:26][CH3:27])[C@@H:17]([O:18]C(=O)C)[C@H:12]1[O:13]C(=O)C.[CH:28]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH:28]1([NH:33][C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:7]=3[N:8]=[CH:9][N:10]=2)[C@@H:11]2[O:23][C@H:22]([CH2:24][O:25][CH2:26][CH3:27])[C@@H:17]([OH:18])[C@H:12]2[OH:13])[CH2:32][CH2:31][CH2:30][CH2:29]1

참가 물질

3

반응물 2

HCID 2906CyclopentylamineHCID 110693776-chloro-9-(2,3-di-O-acetyl-5-O-ethyl-beta-D-ribofuranosyl)-purine

생성물 1

HCID 11122039N6-cyclopentyl-5'-O-ethyladenosine

실험 절차

Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-ethyl-β-D-ribofuranosyl)-purine (62, 502 mg, 1.26 mmol) and cyclopentylamine (1.89 mmol, 187 μL). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 316 mg (0.87 mmol, 69%), mp 134–136° C.; Rf 0.49 (eluens 10% MeOH in CH2Cl2). The product was re-crystallized from CH3CN; 1H NMR (DMSO-d6) δ 8.31 (s, 1H, H-8), 8.19 (s, 1H, H-2), 7.72 (d, 1H, J=7.55 Hz, NH), 5.89 (d, 1H, J=5.15 Hz, H-1′), 5.55–5.25 (m, 2H, OH-2′,3′), 4.53 (t, 1H, J=4.81 Hz, H-2′), 4.15 (t, 1H, J=2.40 Hz, H-3′), 4.01–3.96 (m, 1H, H-4′), 3.62-3.48 (m, 2H, H-5′), 3.46 (q, 2H, J=7.21 Hz, CH2CH3), 1.99–1.82 (m, 2H, cyclopentyl), 1.78–1.52 (m, 4H, cyclopentyl), 1.11 (t, 3H, J=7.21 Hz, CH3); MS m/z 364 (M+H)+; Anal. (C17H25N5O4.0.6 CH3CN) C, H, N.

후처리

  1. customThe mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2)
  2. customThe product was re-crystallized from CH3CN

출처 및 근거

ORD 기록
ord-67dd4af9dd1347f5969c02662dbd86bf
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084127B2

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