Cyclopentylamine → N6-cyclopentyl-2-Chloro-5'-O-ethyladenosine

HRID 6671

반응식

HRID 6671 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:23][C@H:22]([CH2:24][O:25][CH2:26][CH3:27])[C@@H:17]([O:18]C(=O)C)[C@H:12]2[O:13]C(=O)C)=[C:4](Cl)[N:3]=1.[CH:29]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:29]1([NH:34][C:4]2[C:5]3[N:6]=[CH:7][N:8]([C:9]=3[N:10]=[C:2]([Cl:1])[N:3]=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])[CH2:33][CH2:32][CH2:31][CH2:30]1

참가 물질

3

반응물 2

HCID 2906CyclopentylamineHCID 110700822,6-dichloro-9-(2,3-di-O-acetyl-5-O-ethyl-beta-D-ribofuranosyl)-purine

생성물 1

HCID 11003842N6-cyclopentyl-2-Chloro-5'-O-ethyladenosine

실험 절차

Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-ethyl-β-D-ribofuranosyl)-purine (63, 505 mg, 1.16 mmol) and cyclopentylamine (1.74 mmol, 172 μL). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 323 mg (0.81 mmol, 70%), mp 114–116° C.; Rf 0.55 (10% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 8.34 (s, 1H, H-8), 8.32 (bs, 1H, NH), 5.82 (d, 1H, J=5.15 Hz, H-1′), 5.53 (d, 1H, J=5.18 Hz, OH-2′), 5.29 (d, 1H, J=5.15 Hz, OH-3′), 4.47–4.37 (m, 2H, CH, H-2′), 4.11–4.10 (m, 1H, H-3′), 4.00 (q, 1H, J=4.47 Hz, H-4′), 3.62–3.58 (m, 2H, H-5′), 3.47 (q, 2H, J=7.21 Hz, CH2CH3), 2.00–1.83 (m, 2H, cyclopentyl), 1.71–1.51 ((m, 4H, cyclopentyl), 1.12 (t, 3H, J=7.21 Hz, CH3); MS m/z 399 (M+H)+; Anal. (C17H24ClN5O4) C, H, N.

후처리

  1. customThe mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-227c8853310445f6bfa8c4ba4f49e960
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084127B2

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