Methanol → (S)-(-)-N-[[2-Oxo-3-[4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide

HRID 840394Notes

Reaction equation

HRID 840394 reaction equation
C(=O)([O-])O.[Na+].[NH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]3=[O:28])=[CH:14][CH:13]=2)=[CH:8][CH2:7]1.[C:29]([O:32][CH2:33][C:34](Cl)=[O:35])(=[O:31])[CH3:30].CO>CC(C)=O.O.ClCCl>[C:29]([O:32][CH2:33][C:34]([N:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]3=[O:28])=[CH:14][CH:13]=2)=[CH:8][CH2:7]1)=[O:35])(=[O:31])[CH3:30]

Participants

8

Reactant 4

HCID 887MethanolHCID 26297Acetoxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 20638827N-((5S)-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

Product 1

HCID 54460068(S)-(-)-N-[[2-Oxo-3-[4-[1-[(acetoxy)acetyl]-3,6-dihydro-2H-pyridin-4-yl]phenyl]-5-oxazolidinyl]methyl]acetamide

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
1.5 °C

Procedure

Sodium hydrogen carbonate (1.89 g) was added to a stirred solution of Example 2 (1.92 g) in a mixture of acetone (25 ml) and water (12.5 ml), and the mixture cooled to 0-3° C. Acetoxyacetyl chloride (1.23 g, 0.97 ml) was added dropwise over 5-10 mins. and the reaction mixture was stirred at 0-5° C. for 30 minutes then allowed to warm to ambient temperature over 1 hour. TLC (10% methanol in dichloromethane) showed complete reaction. The reaction mixture was diluted with water and extracted well with ethyl acetate. The organic phase was washed with brine and dried over anhydrous sodium sulfate. The title compound crystallized during evaporation of the solvent and was triturated with ether (yield=1.70 g, 91%).

Workup

  1. temperatureto warm to ambient temperature over 1 hour
  2. customreaction
  3. extractionextracted well with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe title compound crystallized during evaporation of the solvent
  7. customwas triturated with ether (yield=1.70 g, 91%)

Sources & evidence

ORD record
ord-a3ab201a19424518a7cdb1ec0fe0c4d1
Source dataset
uspto-grants-2002_04
Patent number
US06365751B1

Reaction notes

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