Methanol → Maribavir

HRID 1421480Notes

Reaction equation

HRID 1421480 reaction equation
[Cl:1][C:2]1[C:32]([Cl:33])=[CH:31][C:5]2[N:6]([C@H:13]3[O:25][C@@H:24]([CH2:26][O:27]C(=O)C)[C@H:19]([O:20]C(=O)C)[C@@H:14]3[O:15]C(=O)C)[C:7]([NH:9][CH:10]([CH3:12])[CH3:11])=[N:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O.CO>C(O)C>[Cl:1][C:2]1[C:32]([Cl:33])=[CH:31][C:5]2[N:6]([C@H:13]3[O:25][C@@H:24]([CH2:26][OH:27])[C@H:19]([OH:20])[C@@H:14]3[OH:15])[C:7]([NH:9][CH:10]([CH3:11])[CH3:12])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10340Sodium CarbonateHCID 53780792HCID 53780792, compound

Product 1

HCID 471161MaribavirYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5,6-Dichloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole (7.50 g, 14.93 mmol), sodium carbonate (1.72 g, 16.23 mmol), water (29 mL), methanol (100 mL) and ethanol (100 mL) were used according to general procedure III. The product was purified by silica gel chromatography using 55:45 dichloromethanelmethanol to afford 4.72 g (84%) of a white foam. Analytical data were consistent with the assigned structure.

Workup

  1. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-50b746d9c2224bec924adf992107661f
Source dataset
uspto-grants-2000_06
Patent number
US06077832

Reaction notes

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