Acetic Acid → 1-(5-O-Acetyl-beta-D-ribofuranosyl)-2,5,6-trichlorobenzimidazole

HRID 724854

反応式

HRID 724854 の反応式
[Cl: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[Cl: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 466019[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,5,6-trichlorobenzimidazol-1-yl)tetrahydrofuran-2-yl]methyl acetateHCID 517044Potassium Acetate

生成物 1

HCID 228765571-(5-O-Acetyl-beta-D-ribofuranosyl)-2,5,6-trichlorobenzimidazole

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

実験手順

A mixture of 42 (0.48 g, 1.0 mmol) and KOAc (0.49 g; 5.0 mmol) in MeOH/H2O (20 mL/2 mL) was stirred at room temperature for 24 h. AcOH (0.286 mL, 5.0 mmol) was added and stirring was Continued at room temperature for 15 min. The reaction mixture was evaporated and the residue was partitioned between H2O/CHCl3 (50 mL/50 mL). The CHCl3 layer was washed with sat. NaCl solution (50 mL), dried (Na2SO4), and evaporated. The residue was chromatographed on a silica column (1.9×20 cm, eluted with CHCl3, 1%, 2%, 4% MeOH/CHCl3). Evaporation of fractions 42-51 (15 mL per fraction) and recrystallization from MeOH gave 0.178 g (2 crops, 45%) of 42a as white crystals. MP: 82°-87° C. MS: (El) m/e 393.9875 (20%, M+ =393.9890). 1H NMR (DMSO-d6): d 8.00, 7.96 (2×s, 2, 7-H and 4-H), 5.91 (d, 1, 1-H, J1'-2' =7.5 Hz), 5.59 (d, 1,2'-OH, J2'-2'OH =6.0 Hz), 5.45 (d, 1, 3'-OH, J3'-3'OH =4.5 Hz), 4.44 (dd, 1, 5'-H, J5'-4' =4.5 Hz, J5'-5' =12.5 Hz), 4.42 (m, 1,2'-H, J2'-3' =6.0 Hz), 4.25 (dd, 1,5"-H, J5"-4' =2.5 Hz), 4.17 (m, 1, 4'-H, J3'-4' =3.5 Hz), 4,11 (m, 1, 3'-H), 2.14 (s, 3, 5'-OAc) 13C NMR (DMSO-d6): d 169.95 (COCH3), 142.03 (C2), 140.92 (C3a), 132.30 (C7a), 125.96, 125.86 (C5 and C6), 120.28 (C4), 113.47 (C7), 89.32 (C1'), 82.63 (C4'), 71.41 (C2'), 69.03 (C3'), 63.35 (C5'). 20.56 (COCH3). Anal. Calcd. for C14H13Cl3N2O5 : C, 42.50; H, 3.31; N, 7.08. Found: C, 42.45; H, 3.20; N, 6.97.

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 H2O/CHCl3 (50 mL/50 mL)
  5. washThe CHCl3 layer was washed with sat. NaCl solution (50 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was chromatographed on a silica column (1.9×20 cm, eluted with CHCl3, 1%, 2%, 4% MeOH/CHCl3)
  9. customEvaporation of fractions 42-51 (15 mL per fraction) and recrystallization from MeOH

出典と根拠

ORDレコード
ord-1a0c5c3adeb54551917ddac9af0e7551
出典データセット
uspto-grants-1998_01
特許番号
US05705490

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