Acetic Acid → HCID 54088500, compound

HRID 1281696Notes

Reaction equation

HRID 1281696 reaction equation
C([O:4][C@@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[CH2:8][O:7][C@H:6]1[N:19]1[C:23]2[CH:24]=[C:25]([Cl:29])[C:26]([Cl:28])=[CH:27][C:22]=2[N:21]=[C:20]1[Cl:30])(=O)C.C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)C>C(O)C.O>[C@@H:6]1([N:19]2[C:23]3[CH:24]=[C:25]([Cl:29])[C:26]([Cl:28])=[CH:27][C:22]=3[N:21]=[C:20]2[Cl:30])[O:7][CH2:8][C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 54322940HCID 54322940, compound

Product 1

HCID 54088500HCID 54088500, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A 100 ml round bottom flask was charged with 1-(2,3,4-Tri-O-acetyl-α-L-lyxopyranosyl)-2,5,6-trichlorobenzimidazole (303 mg, 0.65 mmol) and this was dissolved in 50 ml of an equimolar mixture of ethanol and water. To the stirred solution was added anhydrous sodium carbonate (212 mg, 2.0 mmol) and the reaction mixture allowed to stir at room temperature for 3 hours. The solution was neutralized with acetic acid and the solvent evaporated in vacuo. the resultant solid was dissolved in ethyl acetate and this was washed successively with water, sat. NaHCO3 solution, and sat. NaCl solution (1×50 ml each). The organic layer was dried over sodium sulfate and the solvent evaporated in vacuo to yield, upon vacuum drying, 205 mg (89.1%) of the title compound as a white foam. mp 184-184.5° C. 1H NMR (DMSO-d6, 360 at MHz) δ7.980 (s,1H), 7.922 (s, 1H), 5.644 (d,1H, J=9.26 Hz), 5.489 (d, 1H, J=3.24 Hz), 5.401 (d, 1H, J=3.76 Hz), 5.266 (d, 1H, J=6.52 Hz), 4.245 (m, 1H), 3.924 (d, 1H, J=2.81 Hz), 3.905 (dd, 2H, J=11.64 Hz, J=72.50 Hz). Anal. Calcd. for C, 40.76; H, 3.14; N, 7.92. Found: C, 40.78; H, 3.28; N, 7.75.

Workup

  1. customthe solvent evaporated in vacuo
  2. dissolutionthe resultant solid was dissolved in ethyl acetate
  3. washthis was washed successively with water, sat. NaHCO3 solution, and sat. NaCl solution (1×50 ml each)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent evaporated in vacuo
  6. customto yield, upon vacuum
  7. customdrying

Sources & evidence

ORD record
ord-4a46f3eaaae047959bd2c76b2c740810
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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