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

HRID 6673

反応式

HRID 6673 の反応式
[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][CH:26]3[CH2:28][CH2:27]3)[C@@H:17]([O:18]C(=O)C)[C@H:12]2[O:13]C(=O)C)=[C:4](Cl)[N:3]=1.[CH:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH:30]1([NH:35][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][CH:26]3[CH2:27][CH2:28]3)[C@@H:17]([OH:18])[C@H:12]2[OH:13])[CH2:34][CH2:33][CH2:32][CH2:31]1

参加物

3

反応物 2

HCID 2906CyclopentylamineHCID 111130652,6-dichloro-9-(2,3-di-O-acetyl-5-O-cyclopropyl-beta-D-ribofuranosyl)-purine

生成物 1

HCID 11811662N6-cyclopentyl-2-Chloro-5'-O-cyclopropyladenosine

実験手順

Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-cyclopropyl-β-D-ribofuranosyl)-purine (65, 543 mg, 1.22 mmol) and cyclopentylamine (1.83 mmol, 180 μL). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 400 mg (0.98 mmol, 80%), mp 104–106° C.; Rf 0.51 (10% MeOH in CH2Cl2). The product was re-crystallized from (C2H5)2O; 1H NMR (DMSO-d6) δ 8.34 (bs, 1H, NH), 8.28 (s, 1H, H-8), 5.81 (d, 1H, J=5.15 Hz, H-1′), 5.53 (d, 1H, J=5.84 Hz, OH-2′), 5.29 (d, 1H, J=5.15 Hz, OH-3′), 4.50 (q, 1H, J=5.15 Hz, H-2′), 4.50–4.47 (m, 1H, CH), 4.09–3.99 (m, 2H, H-3′,4′), 3.68–3.63 (m, 2H, H-5′), 1.94–1.89 (m, 2H, cyclopentyl), 1.71-1.50 (m, 4H, cyclopentyl), 0.46–0.41 (m, 4H, OCHCH2CH2); MS m/z 410 (M+H)+; Anal. (C18H24ClN5O4.0.2(C2H5)2O) C, H, N.

後処理

  1. customThe mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2)
  2. customThe product was re-crystallized from (C2H5)2O

出典と根拠

ORDレコード
ord-33f7d48ca5fb4896af7983cbb4253f72
出典データセット
uspto-grants-2006_08
特許番号
US07084127B2

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