Hydrochloric Acid → N6-(3-Iodobenzyl)-5'-O-Ethyladenosine

HRID 6670

反応式

HRID 6670 の反応式
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.[I:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32][NH2:33].Cl>>[I:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32][NH:33][C:2]1[C:3]2[N:4]=[CH:5][N:6]([C:7]=2[N:8]=[CH:9][N:10]=1)[C@@H:11]1[O:23][C@H:22]([CH2:24][O:25][CH2:26][CH3:27])[C@@H:17]([OH:18])[C@H:12]1[OH:13]

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 970123-IodobenzylamineHCID 110693776-chloro-9-(2,3-di-O-acetyl-5-O-ethyl-beta-D-ribofuranosyl)-purine

生成物 1

HCID 10436397N6-(3-Iodobenzyl)-5'-O-Ethyladenosine

実験手順

Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-ethyl-β-D-ribofuranosyl)-purine (62, 367 mg, 0.92 mmol) and 3-iodobenzylamine.HCl (1.38 mmol, 372 mg). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 339 mg (0.66 mmol, 72%), mp 164–166° C.; Rf 0.40 (10% MeOH in CH2Cl2). The product was re-crystallized from CH3CN; 1H NMR (DMSO-d6) δ 8.45 (bs, 1H, NH), 8.37 (s, 1H, H-8), 8.21 (s, 1H, H-2), 7.71 (s, 1H, CCHCI), 7.57 (d, 1H, J=7.90 Hz, CCHCHCH), 7.34 (d, 1H, J=6.52 Hz, CCHCH), 7.09 (t, 1H, J==6.87 Hz, CCHCH), 5.91 (d, 1H, J=4.46 Hz, H-1′), 5.53 (d, 1H, J=5.49 Hz, OH-2′), 5.27 (d, 1H, J=4.80 Hz, OH-3′), 4.67–4.64 (m, 2H, NHCH2), 4.56 (q, 1H, J=4.81 Hz, H-2′), 4.17 (q, 1H, J=4.81 Hz, H-3′), 4.00 (q, 1H, J=4.12 Hz, H-4′), 3.60 (dq, 2H, J=9.61 Hz, J=3.43 Hz, H-5′), 3.47 (q, 2H, J=6.52 Hz, OCH2CH3), 1.12 (t, 3,3 J=6.52 Hz, CH3); MS m/z 512 (M+H)+; Anal. (C19H22IN5O4.0.3 CH3CN) 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 CH3CN

出典と根拠

ORDレコード
ord-f987bac8e4204a08947a7a5ff7139be3
出典データセット
uspto-grants-2006_08
特許番号
US07084127B2

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