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

HRID 219541Notes

Reaction equation

HRID 219541 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-ed98b68429834b1d80c2ebb76cde4afb
Source dataset
uspto-grants-2012_06
Patent number
US08202844B2

Reaction notes

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