Water → HCID 69226066, compound

HRID 433082Notes

Reaction equation

HRID 433082 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-764fded543184bbaa8d7889ab110ee36
Source dataset
uspto-grants-2003_12
Patent number
US06667301B2

Reaction notes

Loading…