Sodium Methoxide → HCID 11791428, compound

HRID 1463038Notes

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 11192185HCID 11192185, compound

Product 1

HCID 11791428HCID 11791428, compoundYield 54.6%

Conditions

Temperature: 0 °C

Procedure

1-(2',3',5'-tri-O-benzoyl-β-D-arabinofuranosyl)-2-nitroimidazole (150 mg, 0.27 mmol) was added to 2.5 ml of 0.025 M methanolic sodium methoxide. The mixture was stirred at 0° C. for three hours and then purified by preparative TLC using chloroform:methanol (6:1) to give 36 mg (54.6%) of the title product as white needles, mp 172° C.

Workup

custompurified by preparative TLC

Sources & evidence

ORD record: ord-6d87b9a37e5a4e33a217f3a10c083ede
Source dataset: uspto-grants-1984_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04462992

Reaction notes

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