Water → HCID 69226066, compound

HRID 900659Notes

Reaction equation

HRID 900659 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[O:15][C:14](=[O:16])[NH:13][C@H:12]2[CH3:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][C:19](C)([O-])C.[K+].ICC.O>CN(C)C=O.O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]2[O:15][C:14](=[O:16])[N:13]([CH2:18][CH3:19])[C@H:12]2[CH3:17])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 23665647Potassium tert-butoxideHCID 69222385(4S,5S)-5-(4-tert-butylphenyl)-4-methyloxazolidin-2-one

Product 1

HCID 69226066HCID 69226066, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1 g (4.3 mmole) (4S,5S)-5-(4-tert-butylphenyl)-4-methyl-oxazolidin-2-one p in 10 mL N,N-dimethylformamide was added 5.2 mL (5.2 mmole) 1 M potassium tert-butoxide in tetrahydrofuran. To the resulting gel was added 0.4 mL (4.7 mmole) iodoethane. The reaction mixture was heated at 70° C. for 1 hr. Cold water (25 mL) was added and the mixture was extracted with 30 mL ethyl acetate. The organic phase was washed with two 10 mL portions water, dried (magnesium sulfate) and concentrated under reduced pressure. (4S,5S)-5-(4-tert-Butylphenyl)-4-methyl-3-ethyl-oxazolidin-2-one q was isolated as a crystalline solid from ethyl acetate/hexane, 1.06 g. M+H=261.

Workup

  1. extractionthe mixture was extracted with 30 mL ethyl acetate
  2. washThe organic phase was washed with two 10 mL portions water
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d011f3c2e3e483da196f81a2690169f
Source dataset
uspto-grants-2008_04
Patent number
US07361648B2

Reaction notes

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