Hydrochloric Acid → 5'-Methanesulfonyl-2',3'-anhydro-5-methyluridine

HRID 975186Notes

Reaction equation

[OH-].[Na+].CS([C@@:7]1([OH:32])[C@:11](S(C)(=O)=O)(O)[C@@H:10]([CH:17]([S:19]([CH3:22])(=[O:21])=[O:20])[OH:18])[O:9][C@H:8]1[N:23]1[CH:30]=[C:29]([CH3:31])[C:27](=[O:28])[NH:26][C:24]1=[O:25])(=O)=O.Cl>>[CH3:22][S:19]([CH:17]([OH:18])[C@H:10]1[O:9][C@@H:8]([N:23]2[CH:30]=[C:29]([CH3:31])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[C@@H:7]2[O:32][C@H:11]12)(=[O:20])=[O:21]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 536894342',3',5'-Tris(methanesulfonyl)-5-methyluridine

Product 1

HCID 867504345'-Methanesulfonyl-2',3'-anhydro-5-methyluridine

Conditions

Temperature: 0 °C

Procedure

To a solution of 49 ml 1N sodium hydroxide was added 2',3',5'-tris(methanesulfonyl)-5-methyluridine (2, 6.0 g). The mixture was stirred at 70°-72° C. for 15 minutes and then cooled 0° C. The pH was adjusted to 4 by using concentrated HCl. The resulting slurry was filtered, washed with 2×10 ml water and dried to give 5'-methanesulfonyl-2'-3'-anhydro-5-methyluridine (3), 3.1 g, (84%).

Workup

filtrationThe resulting slurry was filtered
washwashed with 2×10 ml water
customdried

Sources & evidence

ORD record: ord-698a2a920d3446009cfd22bcaebe0cb8
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05608049

Reaction notes

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