Sodium Carbonate → HCID 54335116, compound

HRID 610455Notes

Reaction equation

HRID 610455 reaction equation
[C:1]([NH:4][C:5]1[N:9]([C@H:10]2[O:22][C@@H:21]([CH2:23][O:24]C(=O)C)[C@H:16]([O:17]C(=O)C)[C@@H:11]2[O:12]C(=O)C)[C:8]2[CH:28]=[C:29]([Cl:33])[C:30]([Cl:32])=[CH:31][C:7]=2[N:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].N[C@]1(O)[C@@H](O)[C@H](C(Cl)O)O[C@@H]1N1C2C=C(Cl)C=CC=2N=C1>CO.C(O)C.O>[C:1]([NH:4][C:5]1[N:9]([C@H:10]2[O:22][C@@H:21]([CH2:23][OH:24])[C@H:16]([OH:17])[C@@H:11]2[OH:12])[C:8]2[CH:28]=[C:29]([Cl:33])[C:30]([Cl:32])=[CH:31][C:7]=2[N:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 54201662HCID 54201662, compoundHCID 86754918HCID 86754918, compound

Product 1

HCID 54335116HCID 54335116, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-acetamido-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole (0.35 g, 0.75 mmol) in methanol (8 mL) and ethanol (8 mL) was combined with a solution of sodium carbonate (0.12 g, 1.1 mmol) in water (2 mL). The solution was stirred at rt for 24 h, then the methanol and ethanol were removed on the rotoevaporator. The solution was then extracted between ethyl acetate (2×150 mL) and saturated NaCl (20 mL). The organics were concentrated and purified by multiple cyclings on a chromatotron, fitted with a 2 mm rotor, using 1:10 methanol:dichloromethane to give a white solid (0.067 g, 0. 18 mmol, 23%); This material was identified by 1H NMR, MS and HPLC, it contained about 7% of 2-amino-5,6-dichloro-beta-L-ribofuranosyl-1H-benzimidazole by 1H NMR. HPLC showed two small (~5%) impurities.

Workup

  1. customthe methanol and ethanol were removed on the rotoevaporator
  2. extractionThe solution was then extracted between ethyl acetate (2×150 mL) and saturated NaCl (20 mL)
  3. concentrationThe organics were concentrated
  4. custompurified by multiple cyclings on a chromatotron
  5. customfitted with a 2 mm rotor
  6. customdichloromethane to give a white solid (0.067 g, 0. 18 mmol, 23%)

Sources & evidence

ORD record
ord-408d6a4feb14414b89a7ef421ae1ac02
Source dataset
uspto-grants-1999_12
Patent number
US05998605

Reaction notes

Loading…