Water → (2R,4S,4 aS)-11-fluoro-2,4-dimethyl-8-(2-(methylsulfonyl)pyrimidin-4-yl)-2,4,4a,6-tetrahydro-1H,1'H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2',4',6'(3'H)-trione

HRID 245566

Reaction equation

HRID 245566 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[F:7][C:8]1[C:9]2[O:34][N:33]=[C:32]([C:35]3[CH:40]=[CH:39][N:38]=[C:37](SC)[N:36]=3)[C:10]=2[CH:11]=[C:12]2[C:25]=1[N:24]1[CH2:26][C@@H:27]([CH3:31])[O:28][C@@H:29]([CH3:30])[C@@H:23]1[C:14]1([C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16][C:15]1=[O:22])[CH2:13]2.[CH2:43]1COCC1.O>CO.C(Cl)Cl>[F:7][C:8]1[C:9]2[O:34][N:33]=[C:32]([C:35]3[CH:40]=[CH:39][N:38]=[C:37]([S:3]([CH3:43])(=[O:5])=[O:2])[N:36]=3)[C:10]=2[CH:11]=[C:12]2[C:25]=1[N:24]1[CH2:26][C@@H:27]([CH3:31])[O:28][C@@H:29]([CH3:30])[C@@H:23]1[C:14]1([C:15](=[O:22])[NH:16][C:17](=[O:21])[NH:18][C:19]1=[O:20])[CH2:13]2

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 67434098(2R,4S,4aS)-11-fluoro-2,4-dimethyl-8-(2-(methylthio)pyrimidin-4-yl)-2,4,4a,6-tetrahydro-1H,1'H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2',4',6'(3'H)-trione

Product 1

HCID 67431840(2R,4S,4 aS)-11-fluoro-2,4-dimethyl-8-(2-(methylsulfonyl)pyrimidin-4-yl)-2,4,4a,6-tetrahydro-1H,1'H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2',4',6'(3'H)-trione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Oxone (5902 mg, 9.60 mmol) was added to a solution of (2R,4S,4aS)-11-fluoro-2,4-dimethyl-8-(2-(methylthio)pyrimidin-4-yl)-2,4,4a,6-tetrahydro-1H,1′H-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5′-pyrimidine]-2′,4′,6′(3′H)-trione (Example 168, 984 mg, 1.92 mmol) in MeOH:THF:H2O (30 ml)(1:1:1), and the mixture was stirred at room temperature for 48 hours. The reaction mixture was diluted with DCM (50 ml), stirred for 10 minutes, filtered, and the filter cake was washed with EtOH. The filtrate was washed with water and brine, concentrated under reduced pressure to give the desired product used in subsequent reactions without further purification.

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with EtOH
  3. washThe filtrate was washed with water and brine
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f3492e58b1044eda4dd86e747110429
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Linked notes

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