Ethanol → HCID 45380498, compound

HRID 245578Notes

Reaction equation

HRID 245578 reaction equation
[F:1][C:2]1[C:3]2[O:28][N:27]=[C:26]([C:29](=[S:31])[NH2:30])[C:4]=2[CH:5]=[C:6]2[C:19]=1[N:18]1[CH2:20][C@@H:21]([CH3:25])[O:22][C@@H:23]([CH3:24])[C@@H:17]1[C:8]1([C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10][C:9]1=[O:16])[CH2:7]2.CCO.Br[CH2:36][C:37](=O)[C:38]([O:40][CH2:41][CH3:42])=[O:39]>CN(C=O)C>[F:1][C:2]1[C:3]2[O:28][N:27]=[C:26]([C:29]3[S:31][CH:36]=[C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[N:30]=3)[C:4]=2[CH:5]=[C:6]2[C:19]=1[N:18]1[CH2:20][C@@H:21]([CH3:25])[O:22][C@@H:23]([CH3:24])[C@@H:17]1[C:8]1([C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10][C:9]1=[O:16])[CH2:7]2

Participants

5

Reactant 3

HCID 702EthanolHCID 66144Ethyl bromopyruvateHCID 87398339HCID 87398339, compound2×

Product 1

HCID 45380498HCID 45380498, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of (2R,4S,4aS)-rel-11-fluoro-2,4-dimethyl-2′,4′,6′-trioxo-1,1′,2,3′,4,4′,4a,6′-octahydro-2′H,6H-spiro[1,4-oxazino[4,3-a][1,2]oxazolo[4,5-g]quinoline-5,5′-pyrimidine]-8-carbothioamide (Intermediate 575, 54 mg, 0.128 mmol) in mixture of EtOH:DMF (1 mL: 0.5 mL) were added ethyl bromopyruvate (47 mg, 0.24 mmol) and molecular sieves, and the mixture was stirred at 100° C. for 12 hours. The reaction mixture was concentrated, the residue was purified by silica gel column chromatography to give product as solid. Yield: 13 mg (20%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography
  3. customto give product as solid

Sources & evidence

ORD record
ord-fc7513436c0e47fbbe6203da577c9749
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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