Sodium Methoxide → 1-[2,5,6-Trichloro-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-indol-3-yl]-ethanone

HRID 28364Notes

Reaction equation

HRID 28364 reaction equation
[Cl:1][C:2]1[N:3]([C@@H:16]2[O:30][C@H:29]([CH2:31][O:32]C(C3C=CC(C)=CC=3)=O)[C@@H:18]([O:19]C(C3C=CC(C)=CC=3)=O)[CH2:17]2)[C:4]2[C:9]([C:10]=1[C:11](=[O:13])[CH3:12])=[CH:8][C:7]([Cl:14])=[C:6]([Cl:15])[CH:5]=2.C[O-].[Na+]>CO>[Cl:1][C:2]1[N:3]([C@@H:16]2[O:30][C@H:29]([CH2:31][OH:32])[C@@H:18]([OH:19])[CH2:17]2)[C:4]2[C:9]([C:10]=1[C:11](=[O:13])[CH3:12])=[CH:8][C:7]([Cl:14])=[C:6]([Cl:15])[CH:5]=2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 671000122,5,6-Trichloro-3-acetyl-1-[3,5-di-o-(p-toluoyl)-2-deoxy-beta-d-ribofuranosyl]indole

Product 1

HCID 52726191-[2,5,6-Trichloro-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-indol-3-yl]-ethanoneYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,5,6-Trichloro-3-acetyl-1-[3,5-di-O-(p-toluoyl)-2-deoxy-β-D-ribofuranosyl]indole (4.116, 0.62 g, 1.0 mmol) was suspended in dry MeOH (50 mL) to which was added sodium methoxide (220 mg, 4.1 mmol). The suspension was stirred at room temperature for 16 h, after which time the solution first clarified and a precipitate then formed. The suspension was allowed to stand at 4° C. for 4 h, and was then filtered, and the solids rinsed with cold MeOH (10 mL). The solid was recrystallized from warm MeOH to yield 0.28 g (74%) of 4.117 as a white crystalline solid: mp dec. >200 C; Rf 0.4 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.52 (s, 1H), 8.37 (s, 1H), 6.49 (dd, 1H), 5.43 (s, 1H, D2O exch.), 5.26 (s, 1H, D2O exch.), 4.45 (m, 1H), 3.89 (d, 1H), 3.72 (m, 2H), 2.60 (s, 3H), 2.49 (m, 1H), 2.13 (m, 1H). 13C-NMR (125 MHz, DMSO-d6): δ 192.13, 132.15, 131.99, 126.12, 125.50, 125.65, 121.96, 115.25, 112.85, 87.55, 85.43, 69.81, 60.67, 47.10, 30.68. HRMS (EI) m/z calcd. for C15H14Cl3NO4 376.9988, found 376.9982. Anal calcd for C15H14Cl3NO4: C, 47.58; H, 3.73; N, 3.70. Found: C, 47.52; H, 3.95; N, 3.59.

Workup

  1. customa precipitate then formed
  2. waitto stand at 4° C. for 4 h
  3. filtrationwas then filtered
  4. washthe solids rinsed with cold MeOH (10 mL)
  5. customThe solid was recrystallized
  6. temperaturefrom warm MeOH

Sources & evidence

ORD record
ord-482e9083444c4f37aba81cb8d9d205a7
Source dataset
uspto-grants-2008_09
Patent number
US07419963B2

Reaction notes

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