Methanol → 1-(2-Oxo-ethyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide

HRID 1259391Notes

Reaction equation

HRID 1259391 reaction equation
N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=O.[Na+].[F:15][C:16]1[CH:21]=[C:20]([I:22])[CH:19]=[CH:18][C:17]=1[NH:23][C:24]1[C:25]([NH:35][S:36]([C:39]2([CH2:42][CH:43]=C)[CH2:41][CH2:40]2)(=[O:38])=[O:37])=[C:26]2[O:34][CH2:33][CH2:32][N:27]2[C:28](=[O:31])[C:29]=1[CH3:30].C[OH:46]>O1CCOCC1.O.C(Cl)Cl.[Os](=O)(=O)(=O)=O>[F:15][C:16]1[CH:21]=[C:20]([I:22])[CH:19]=[CH:18][C:17]=1[NH:23][C:24]1[C:25]([NH:35][S:36]([C:39]2([CH2:42][CH:43]=[O:46])[CH2:40][CH2:41]2)(=[O:37])=[O:38])=[C:26]2[O:34][CH2:33][CH2:32][N:27]2[C:28](=[O:31])[C:29]=1[CH3:30]

Participants

9

Reactant 4

HCID 887MethanolHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 583805551-Allyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide

Product 1

HCID 583805691-(2-Oxo-ethyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amideYield 63%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Osmium tetra oxide (8 mg, 0.035 mmol), 2,6-lutidine (0.08 g, 0.74 mmol) and sodium periodate (0.3 g, 0.001 mol) were added to a solution of 1-allyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide (0.19 g, 0.35 mmol) in dioxane (7 mL) and water (2 mL). The resulting mixture was stirred at room temperature for 5 hours. The reaction was monitored by TLC (5% MeOH in DCM). The reaction mixture was partitioned between ethylacetate and water. The organic layer was washed with water, brine solution, dried over Na2SO4, filtered and the filtrate was concentrated. Purification by column chromatography on silica gel (2% MeOH in DCM) afforded 0.12 g of the product (63% yield). LCMS: m/z=549 (M+1)

Workup

  1. customThe reaction mixture was partitioned between ethylacetate and water
  2. washThe organic layer was washed with water, brine solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customPurification by column chromatography on silica gel (2% MeOH in DCM)

Sources & evidence

ORD record
ord-3e2ebceb86e245cfb48ac85afbff0e82
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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