Acetic Anhydride → HCID 13556431, compound

HRID 1981933Notes

Reaction equation

[C@@H:1]1([C:10]2[Se:11][CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=2)[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3].C(O[C:22](=[O:24])[CH3:23])(=O)C>>[C:2]([O:3][C@@H:2]1[C@H:4]([O:5][C:4](=[O:5])[CH3:6])[C@@H:6]([CH2:8][O:9][C:22](=[O:24])[CH3:23])[O:7][C@H:1]1[C:10]1[Se:11][CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=1)(=[O:3])[CH3:1]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 100665Selenazofurin

Product 1

HCID 13556431HCID 13556431, compound

Procedure

A mixture of 2-β-D-ribofuranosylselenazole-4-carboxamide (1.0 g, 3.25 mmol), N,N-dimethylaminopyridine (catalyst, 80 mg) and acetic anhydride (15 ml) was stirred at room temperature for 3 hours. The solvent was evaporated in vacuo and coevaporated with water (10 ml×2) to provide COMPOUND 3 as a white crystalline product which was triturated with water and collected by filtration. The product was recrystallized from water containing a few drops of ethanol to provide white needles: yield 1.2 g (85 percent), mp 117-119 degrees C. Analysis calculated for C15H18N2O8Se: C, 41.58; H, 4.19; N, 6.47; Se, 18.22. Found: C, 41.80; H, 4.30; N, 6.58; Se, 17.97. Corresponding 2', 3', 5'-O-acyl compounds of the invention are prepared from COMPOUND 1 by this procedure by reacting the latter with the appropriate acid anhydride until the reaction is complete and isolating the product in pure form.

Workup

customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-02a289191fae4c7dbd73fb36e40d3123
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04594416

Reaction notes

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