Ammonia → (2R,3R,4S,5R)-2-(2-amino-5,6-dichloro-benzimidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

HRID 2289466

反応式

HRID 2289466 の反応式
Cl[C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1.[NH3:31]>CO>[NH2:31][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1

参加物

4

反応物 2

HCID 222Ammonia2 回HCID 466019[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,5,6-trichlorobenzimidazol-1-yl)tetrahydrofuran-2-yl]methyl acetate

生成物 1

HCID 466018(2R,3R,4S,5R)-2-(2-amino-5,6-dichloro-benzimidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2,5,6-Trichloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)benzimidazole (42, 0.48 g; 1 mmole) was dissolved in dry MeOH (10 ml). Liq. NH3 (10 ml) was added and the mixture heated in a steel bomb at 100° C. for 2 hr. This mixture was stirred at room temperature for 24 hr. Excess NH3 was allowed to evaporate and the solution evaporated to dryness, absorbed onto silica gel (2 g), and chromatographed on a silica gel column using silica gel (20 g; 60-200 mesh). Elution of the column with CH2Cl2 :CH3OH (96:4) gave the desired compound 44 as the major nucleoside. Evaporation of the solvent and crystallization of the residue from EtOH gave 44 (0.02 g; yield 6.06%). mp. 145° C.; UV Imax (MeOH): 259 (7941) and 301 (8348) nm; Imax (pH1): 215 (26000) and 292 (7520) nm; Imax (pH11): 257 (7967) and 298 (7107) nm. 1H NMR(DMSO-d6): d 8.70 (s,1H, C7 -H, 8.28 (s, 1-H, C4 -H), 7.90 (bs, 2H, D2O exchangeable, NH2), 6.75 (d, C1'H, J1'-2' =4.5 Hz) and the rest of the sugar protons.

後処理

  1. customto evaporate
  2. customthe solution evaporated to dryness
  3. customabsorbed onto silica gel (2 g)
  4. customchromatographed on a silica gel column
  5. washElution of the column with CH2Cl2 :CH3OH (96:4)

出典と根拠

ORDレコード
ord-6d5c06acc61c450abeb07170cc1b2def
出典データセット
uspto-grants-2000_07
特許番号
US06093698

関連ノート

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