Acetic Acid → tert-Butyl {(3R)-1-[5-(2-chlorobenzyl)-7-cyano-3-methyl-2-(methylsulfonyl)-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

HRID 1819296Notes

Reaction equation

[Cl:1][C:2]1[CH:37]=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10]([S:16][CH3:17])=[N:9][C:8]=2[C:7]([C:18]#[N:19])=[C:6]1[N:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:21]1.C(O)(=O)C.[OH2:42].[OH:43]O>CO.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[Cl:1][C:2]1[CH:37]=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10]([S:16]([CH3:17])(=[O:43])=[O:42])=[N:9][C:8]=2[C:7]([C:18]#[N:19])=[C:6]1[N:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:21]1

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium tungstate dihydrate (139 mg) was added to a solution of tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-cyano-3-methyl-2-(methylthio)-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (230 mg) in a mixture of methanol (2 ml), acetic acid (0.7 ml) and water (0.25 ml), and the resulting mixture was heated to 50° C. A 30% aqueous hydrogen peroxide solution (0.29 ml) was added dropwise thereto, followed by stirring at 60° C. for 4 hours. After the reaction mixture was allowed to cool, the precipitate formed was collected by filtration, washed with water and then dried under reduced pressure to obtain the title compound (230 mg) as a white solid.

Workup

temperatureto cool
customthe precipitate formed
filtrationwas collected by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-0accd3d40d384e61bbfc9af04104f043
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601728B2

Reaction notes

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