Acetic Acid → Maribavir Impurity 57

HRID 263873

反応式

HRID 263873 の反応式
[Br:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[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.CC([O-])=O.[K+].CC(O)=O>CO.O>[C:22]([O:21][CH2:20][C@H:18]1[O:19][C@@H:7]([N:6]2[C:5]3[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=3[N:3]=[C:2]2[Br:1])[C@H:8]([OH:9])[C@@H:13]1[OH:14])(=[O:24])[CH3:23]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 466020[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2-bromo-5,6-dichloro-benzimidazol-1-yl)tetrahydrofuran-2-yl]methyl acetateHCID 517044Potassium Acetate

生成物 1

HCID 22876558Maribavir Impurity 57

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

実験手順

A mixture of 52a (1.048 g, 2.0 mmol) and KOAc (0.98 g, 10.0 mmol) in MeOH/H2O (40 mL/4 mL) was stirred at room temperature for 24 hr. AcOH (0.572 mL, 10.0 mmol) was added and stirring was continued at room temperature for 15 min. The reaction mixture was evaporated and the residue was partitioned between EtOAc/H2O (75 mL/75 mL). The EtOAc layer was washed with sat. NaCl solution (75 mL), dried (Na2SO4), and evaporated. The residue was chromatographed on a silica column (1.9×24 cm, eluted with CHCl3, 2%, 3%, 4% MeOH/CHCl3). Evaporation of fractions 15-27 (15 mL per fraction) and recrystallization from MeOH gave 0.50 g (2 crops, 57%) of 52b as white crystals. MP: 85°-95° C. (melted slowly over a large range) MS: (EI) m/e 437.9398 (15%, M+ =437.9385).

後処理

  1. stirringstirring
  2. waitwas continued at room temperature for 15 min
  3. customThe reaction mixture was evaporated
  4. customthe residue was partitioned between EtOAc/H2O (75 mL/75 mL)
  5. washThe EtOAc layer was washed with sat. NaCl solution (75 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was chromatographed on a silica column (1.9×24 cm, eluted with CHCl3, 2%, 3%, 4% MeOH/CHCl3)
  9. customEvaporation of fractions 15-27 (15 mL per fraction) and recrystallization from MeOH

出典と根拠

ORDレコード
ord-927e1d509b6c4ec89c5fc91f5211e5f0
出典データセット
uspto-grants-1997_07
特許番号
US05646125

関連ノート

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