Water → HCID 69933895, compound

HRID 1017253Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[O:17][C@@H:16]([CH2:18][OH:19])[C@H:14]([OH:15])[C@@H:12]2[OH:13])=[C:4]([S:20][NH2:21])[N:3]=1.O.C1C=C(Cl)C=C(C(OO)=[O:31])C=1>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[O:17][C@@H:16]([CH2:18][OH:19])[C@H:14]([OH:15])[C@@H:12]2[OH:13])=[C:4]([S:20]([NH2:21])=[O:31])[N:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A mixture of 2-amino-9-(β-L-ribofiiranosyl)purine-6-sulfenamide 17 (200 mg, 0.637 mmol), ethanol (90 mL) and water (6.4 mL) was vigorously stirred at −10° C. in a salt-ice bath. A solution of MCPBA (80%, 137.0 mg, 0.637 mmol) in ethanol 5.5 mL was added dropwise over a period of 15 minutes. The mixture was allowed to stir and warm as the ice melt (8 h), and stirred at ambient temperature for addition 14 h. A small amount of precipitate was filtered out and the filtrate evaporated at 23° C. to dryness. The residue was triturated with ethyl ether (30 mL) and the solid was collected by filtration, washed with ethyl ether (10 mL). The solid was again suspended in ethyl ether (25 mL), filtered, and dried to give 182 mg (87%) of 2-amino-9-(β-L-ribofuranosyl)purine-6-sulfinamide 18 as a colorless solid.

Workup

stirringto stir
custom(8 h)
stirringstirred at ambient temperature for addition 14 h
filtrationA small amount of precipitate was filtered out
customthe filtrate evaporated at 23° C. to dryness
customThe residue was triturated with ethyl ether (30 mL)
filtrationthe solid was collected by filtration
washwashed with ethyl ether (10 mL)
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-f8234b5dcf1a4230a343de70dc185af2
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479463B1

Reaction notes

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