Methanol → 1-(2,3-Dihydroxy-propyl)-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 1259393Notes

Reaction equation

HRID 1259393 reaction equation
CN1CCOCC1.[OH2:8].[F:9][C:10]1[CH:15]=[C:14]([I:16])[CH:13]=[CH:12][C:11]=1[NH:17][C:18]1[C:19]([NH:29][S:30]([C:33]2([CH2:36][CH:37]=[CH2:38])[CH2:35][CH2:34]2)(=[O:32])=[O:31])=[C:20]2[O:28][CH2:27][CH2:26][N:21]2[C:22](=[O:25])[C:23]=1[CH3:24].C[OH:40]>C1COCC1.C(Cl)Cl.[Os](=O)(=O)(=O)=O>[F:9][C:10]1[CH:15]=[C:14]([I:16])[CH:13]=[CH:12][C:11]=1[NH:17][C:18]1[C:19]([NH:29][S:30]([C:33]2([CH2:36][CH:37]([OH:40])[CH2:38][OH:8])[CH2:34][CH2:35]2)(=[O:32])=[O:31])=[C:20]2[O:28][CH2:27][CH2:26][N:21]2[C:22](=[O:25])[C:23]=1[CH3:24]

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 79724-MethylmorpholineHCID 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 529340941-(2,3-Dihydroxy-propyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amideYield 11%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Osmium tetra oxide (8 mg, 0.003 mmol), N-methyl morpholine (8 mg, 0.068 mmol) and water (0.5 mL) were added to a stirred 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 (I-9a: 0.04 g, 0.073 mmol) in THF (5 mL). The resulting mixture was stirred at room temperature overnight. 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 and concentrated. Purification by thin layer chromatography on silica gel (5% MeOH in DCM) afforded 0.005 g of the product (11% yield).

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. concentrationconcentrated
  5. customPurification by thin layer chromatography on silica gel (5% MeOH in DCM)

Sources & evidence

ORD record
ord-4fdc7575ae2a4f228a8fffb3fab8ee9a
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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