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

HRID 263870

반응식

HRID 263870 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

실험 절차

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: (EI) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-cc9d070d817945b98495bb5e84dc6806
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646125

연결된 노트

불러오는 중…