Sodium Chloride → HCID 18658173, compound

HRID 1768854Notes

Reaction equation

HRID 1768854 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([C@H:20]1[CH2:24][O:23][C:22](=[O:25])[N:21]1[C:26](=[O:35])[CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Br[CH2:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39].[Cl-].[Na+]>CCCCCC.O1CCCC1>[CH2:13]([C@H:20]1[CH2:24][O:23][C:22](=[O:25])[N:21]1[C:26](=[O:35])[C@H:27]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 62576Benzyl bromoacetateHCID 10957844(S)-4-BENZYL-3-(3-PHENYLPROPANOYL)OXAZOLIDIN-2-ONEHCID 178418339Butyllithium

Product 1

HCID 18658173HCID 18658173, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

2.91 ml (20.8 mmole) of diisopropylamine and 13.40 ml (21.4 mmole) of butyllithium (as a 1.6M solution in hexane) were added, at -78° C. and under an atmosphere of nitrogen, to 50 ml of anhydrous tetrahydrofuran, and the mixture was stirred for 30 minutes. A solution of 5.35 g (17.3 mmole) of (4S)-(-)-4-benzyl-N-(3-phenylpropionyl)-2-oxazolidinone in 20 ml of anhydrous tetrahydrofuran was added to the resulting mixture, and then the mixture was stirred at the same temperature for 1 hour. At the end of this time, a solution of 5.74 ml (36.2 mmole) of benzyl bromoacetate in 10 ml of anhydrous tetrahydrofuran was added dropwise to the mixture, and then the mixture was stirred for 3 hours. At the end of this time, a saturated aqueous solution of sodium chloride was added to the mixture, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated by distillation under reduced pressure. The residue was purified by medium pressure column chromatography through silica gel (using a 1:5 by volume mixture of ethyl acetate and hexane as the eluent) to afford 5.47 g (yield 69%) of the title compound as a colorless oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. stirringthe mixture was stirred for 3 hours
  3. extractionwas then extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated by distillation under reduced pressure
  6. customThe residue was purified by medium pressure column chromatography through silica gel (
  7. additionby volume mixture of ethyl acetate and hexane as the eluent)

Sources & evidence

ORD record
ord-01eb33d49bd94eba85c65287dd085a49
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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