Ammonium Chloride → HCID 10108681, compound

HRID 2217344Notes

Reaction equation

HRID 2217344 reaction equation
C([Li])CCC.[CH3:6][C@@H:7]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:10][C:9](=[O:18])[NH:8]1.[Br:19][CH2:20][C:21](Cl)=[O:22].[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>CCCCCC.O1CCCC1>[Br:19][CH2:20][C:21]([N:8]1[C@H:7]([CH3:6])[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:10][C:9]1=[O:18])=[O:22]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 89602Bromoacetyl chlorideHCID 516892Sodium BicarbonateHCID 2733812(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 10108681HCID 10108681, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

117 ml of a 1.6 molar solution of butyllithium in hexane is added to a solution of 30.1 g of (4R,5S)-4-methyl-5-phenyloxazolidin-2-one in 500 ml of tetrahydrofuran within 30 minutes at −70° C. under nitrogen. Then, a solution of 26.8 g of bromoacetyl chloride in 250 ml of tetrahydrofuran is added in drops in such a way that the temperature does not exceed −65° C. After 1.75 hours of stirring at −70° C., a saturated ammonium chloride solution is added, followed by 60 ml of a saturated sodium bicarbonate solution, and it is allowed to come to 25° C. After the phases are separated, the aqueous phase is extracted twice with 100 ml of ether each. The combined organic phases are washed with semiconcentrated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum after filtration. The residue that is thus obtained is purified by chromatography on silica gel. With hexane/0-50% ether, 34.8 g of the title compound is obtained as a colorless oil.

Workup

  1. customdoes not exceed −65° C
  2. customto come to 25° C
  3. customAfter the phases are separated
  4. extractionthe aqueous phase is extracted twice with 100 ml of ether each
  5. washThe combined organic phases are washed with semiconcentrated sodium chloride solution
  6. customdried on sodium sulfate
  7. concentrationconcentrated by evaporation in a vacuum
  8. filtrationafter filtration
  9. customThe residue that is thus obtained
  10. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-32f8ed9e06aa441688a6f27678b2f662
Source dataset
uspto-grants-2008_08
Patent number
US07407975B2

Reaction notes

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