Sodium Methoxide → HCID 15591832, compound

HRID 1463037Notes

Reaction equation

C([O:9][C@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[CH:38]=[CH:37][N:36]=[C:35]1[N+:39]([O-:41])=[O:40])(=O)C1C=CC=CC=1.C[O-].[Na+]>>[C@H:11]1([N:34]2[CH:38]=[CH:37][N:36]=[C:35]2[N+:39]([O-:41])=[O:40])[O:12][C@H:13]([CH2:24][OH:25])[C@@H:14]([OH:15])[C@@H:10]1[OH:9]

Participants

Reactant 2

HCID 10942334Sodium Methoxide

HCID 11786241HCID 11786241, compound

Product 1

HCID 15591832HCID 15591832, compoundYield 46.9%

Conditions

Temperature: 0 °C

Procedure

1-(2',3',5'-tri-O-benzoyl-α-D-arabinofuranosyl)-2-nitroimidazole (557 mg, 1 mmol) was added to 5 ml of 0.05 M methanolic sodium methoxide. The mixture was stirred at 0° C. for 2.5 hours. The precipitate of 1-(mono-benzoyl-α-D-arabino furanosyl)-2-nitroimidazole was filtered off and the filtered solution was purified by preparative TLC using chloroform:methanol (5:1) to give 115 mg (46.9%) of the title product as pale yellow needles, mp 160° C.

Workup

filtrationThe precipitate of 1-(mono-benzoyl-α-D-arabino furanosyl)-2-nitroimidazole was filtered off
customthe filtered solution was purified by preparative TLC

Sources & evidence

ORD record: ord-7e8d70f822d54754b6c1148491629a75
Source dataset: uspto-grants-1984_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04462992

Reaction notes

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