Triethylamine → (5S)-5-(Aminomethyl)-3-[4-(2-oxo-1-pyrrolidinyl)phenyl]-1,3-oxazolidin-2-one

HRID 1796944

Reaction equation

HRID 1796944 reaction equation
CS(Cl)(=O)=O.O[CH2:7][C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])=[CH:16][CH:15]=2)[CH2:9]1.C([N:28](CC)CC)C.[K].C1(=O)NC(=O)C2=CC=CC=C12.O.NN.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:28][CH2:7][C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])=[CH:16][CH:15]=2)[CH2:9]1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 11666276(5R)-5-(hydroxymethyl)-3-[4-(2-oxo-1-pyrrolidinyl)phenyl]-1,3-oxazolidin-2-oneHCID 24194345Phthalimide potassium salt

Product 1

HCID 11666268(5S)-5-(Aminomethyl)-3-[4-(2-oxo-1-pyrrolidinyl)phenyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., methanesulfonyl chloride (1.79 g, 15.64 mmol) is added to a solution of (5R)-5-(hydroxymethyl)-3-[4-(2-oxo-1-pyrrolidinyl)phenyl]-1,3-oxazolidin-2-one (3.6 g, 13.0 mmol) and triethylamine (2.9 g, 28.7 mmol) in dichloromethane (160 ml). The reaction mixture is stirred at 0° C. for 1.5 hours and at room temperature for 3 hours and then washed with water, and the aqueous phase is reextracted with dichloromethane. The combined organic phases are dried (magnesium sulfate), filtered and concentrated under reduced pressure. The residue (1.67 g) is then dissolved in acetonitrile (70 ml), phthalimide potassium (2.62 g, 14.16 mmol) is added and the mixture is stirred in a closed vessel in a microwave oven at 180° C. for 45 min. Insoluble residue is removed from the mixture by filtration, the filtrate is evaporated under reduced pressure, the residue (1.9 g) is dissolved in methanol and hydrazine hydrate (0.47 g, 9.37 mmol) is added. The reaction mixture is heated under reflux for 2 hours and cooled, saturated sodium bicarbonate solution is added and the mixture is extracted six times with methylene chloride (2 l in total). The combined organic phases are dried (magnesium sulfate), filtered and concentrated under reduced pressure.

Workup

  1. washwashed with water
  2. dry with materialThe combined organic phases are dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue (1.67 g) is then dissolved in acetonitrile (70 ml)
  6. stirringthe mixture is stirred in a closed vessel in a microwave oven at 180° C. for 45 min
  7. customInsoluble residue is removed from the mixture by filtration
  8. customthe filtrate is evaporated under reduced pressure
  9. dissolutionthe residue (1.9 g) is dissolved in methanol
  10. temperatureThe reaction mixture is heated
  11. temperatureunder reflux for 2 hours
  12. temperaturecooled
  13. extractionthe mixture is extracted six times with methylene chloride (2 l in total)
  14. dry with materialThe combined organic phases are dried (magnesium sulfate)
  15. filtrationfiltered
  16. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c51fbb98e2674f9f81930358ca172368
Source dataset
uspto-grants-2006_04
Patent number
US07034017B2

Linked notes

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