2,6-Lutidine → HCID 86664506, compound

HRID 1186765Notes

Reaction equation

HRID 1186765 reaction equation
[CH2:1]([C:4]1([S:7]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[C:14](=[O:18])[N:13]([CH3:19])[C:12]=2[N:20]([C:28]2[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=2[F:35])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=C.CC1C=CC=C(C)N=1.[O:44]1CCOCC1>O.O=[Os](=O)(=O)=O>[CH3:19][N:13]1[C:14](=[O:18])[C:15]([CH3:17])=[CH:16][C:11]([NH:10][S:7]([C:4]2([CH2:1][CH:2]=[O:44])[CH2:6][CH2:5]2)(=[O:8])=[O:9])=[C:12]1[N:20]([C:28]1[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=1[F:35])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 312751,4-DioxaneHCID 66701564HCID 66701564, compound

Product 1

HCID 86664506HCID 86664506, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 3-(1-allylcyclopropanesulfonamido)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-2-yl(2-fluoro-4-iodophenyl)carbamate (2.370 g, 3.838 mmol) in dioxane (38.4 ml) under a nitrogen atmosphere was added H2O (7.7 ml). Then NalO4 (4 eq, 3.284 g, 15.353 mmol) and 2,6-dimethyl pyridin (2 eq, 0.894 ml, 7.676 mmol) were added and the mixture was cooled to 0° C. At this temperature OsO4 (4% in t-butanol, 0.04 eq, 1,925 ml, 0.154 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 and washed with water, which dissolved the precipitate. The filtrate was extracted twice with ethyl acetate, washed once with brine, dried and concentrated in vacuo. The residue was purified by flash chromatography (Biotage system) to afford the title compound (1.92 g, 79%) as a mixture of the aldehyde and a cyclised 1,2-thiazolidin-3-ol 1,1-dioxide form.

Workup

  1. customto come to room temperature
  2. customto form a fine suspension
  3. stirringAfter stirring for 30 min the precipitate
  4. filtrationwas filtered off
  5. washwashed with water, which
  6. dissolutiondissolved the precipitate
  7. extractionThe filtrate was extracted twice with ethyl acetate
  8. washwashed once with brine
  9. customdried
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography (Biotage system)

Sources & evidence

ORD record
ord-5a5c15b105e94440a503a64162cd83f1
Source dataset
uspto-grants-2014_03
Patent number
US08673919B2

Reaction notes

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