2,6-Lutidine → HCID 86664507, compound

HRID 1186770Notes

Reaction equation

[CH2:1]([C:4]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14](=[O:17])[N:13]([CH3:18])[C:12]=2[N:19]([C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=C.CC1C=CC=C(C)N=1.[O:43]1CCOCC1>O.O=[Os](=O)(=O)=O>[F:34][C:28]1[CH:29]=[C:30]([I:33])[CH:31]=[CH:32][C:27]=1[N:19]([C:12]1[N:13]([CH3:18])[C:14](=[O:17])[CH:15]=[CH:16][C:11]=1[NH:10][S:7]([C:4]1([CH2:1][CH:2]=[O:43])[CH2:5][CH2:6]1)(=[O:9])=[O:8])[C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl (3-{[(1-allylcyclopropyl)sulfonyl]amino}-1-methyl-6-oxo-1,6-dihydropyridin-2-yl)(2-fluoro-4-iodophenyl)carbamate (140 mg, 0.232 mmol) in dioxane (2.30 ml) under a nitrogen atmosphere was added H2O (0.51 ml). Then NaIO4 (4 eq, 198 mg, 0.928 mmol) and 2,6-dimethyl pyridin (2 eq, 0.054 ml, 0.464 mmol) were added and the mixture was cooled to 0° C. At this temperature OsO4 (4% in H2O, 0.05 eq, 71 μl, 0.012 mmol) was added. The mixture was allowed to come to room temperature and then stirred for 18 hours. The mixture was diluted with H2O (4 ml) to form a fine suspension. After stirring for 30 min the precipitate was filtered off to afford the title compound (140 mg, 88%) in sufficient purity for the next transformation (88% UV) as a mixture of the aldehyde and a cyclised 1,2-thiazolidin-3-ol 1,1-dioxide form.

Workup

customto come to room temperature
customto form a fine suspension
stirringAfter stirring for 30 min the precipitate
filtrationwas filtered off

Sources & evidence

ORD record: ord-4494ea46555a4e8cbb6c3810cd590a54
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673919B2

Reaction notes

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