Hydrochloric Acid → HCID 11010755, compound

HRID 2380124Notes

Reaction equation

HRID 2380124 reaction equation
C([Li])CCC.[CH:6]([C@H:9]1[CH2:13][O:12][C:11](=[O:14])[NH:10]1)([CH3:8])[CH3:7].[C:15](Cl)(=[O:24])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.[Cl-].[Na+]>O1CCCC1.CCCCCC>[CH:6]([C@@H:9]1[CH2:13][O:12][C:11](=[O:14])[N:10]1[C:15](=[O:24])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:8])[CH3:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 64801Benzenepropanoyl chlorideHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 11010755HCID 11010755, compoundYield 69,995.297%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

68.3 ml of butyllithium (as a 1.6M hexane solution) were added dropwise, at -78° C. and under an atmosphere of nitrogen, to a solution of 11.75 g (91.0 mmoles) of 4(S)-isopropyl-2-oxazolidinone in 200 ml of anhydrous tetrahydrofuran. The mixture was stirred for 30 minutes, and then a solution of 18.41 g (0.11 mmoles) of dihydrocinnamoyl chloride in 100 ml of anhydrous tetrahydrofuran was added dropwise over a period of 10 minutes. The mixture was then stirred for a further 1 hour, after which 100 ml of 1N aqueous hydrochloric acid and 100 ml of a saturated aqueous solution of sodium chloride were added to the reaction mixture, which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (using a 1:4 by volume mixture of ethyl acetate and hexane as eluent), followed by recrystallization from diisopropyl ether, to give 20.12 g (yield 85%) of the title compound as white crystals, melting at 62°-63° C.

Workup

  1. stirringThe mixture was then stirred for a further 1 hour
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue was purified by medium pressure silica gel column chromatography (
  6. additionby volume mixture of ethyl acetate and hexane as eluent),
  7. customfollowed by recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-07e5441e306c406aa4521e855ad10425
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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