Ammonium Chloride → (4S)-4-benzyl-3-(5-phenylpentanoyl)-1,3-oxazolidin-2-one

HRID 254925Notes

Reaction equation

HRID 254925 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 109654605-phenylpentanoyl ChlorideHCID 178418339Butyllithium

Product 1

HCID 10783156(4S)-4-benzyl-3-(5-phenylpentanoyl)-1,3-oxazolidin-2-oneYield 109.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a tetrahydrofuran (300 ml) solution of (4S)-4-benzyl-1,3-oxazolidin-2-one (26.58 g), 1.58 M of n-butyl lithium (tetrahydrofuran solution; 100 ml) was added under argon atmosphere at −78° C., and the mixture was stirred at the same temperature for 40 minutes. To the mixture, a tetrahydrofuran (100 ml) solution of 5-phenylpentanoyl chloride (32.4 g) was added, followed by stirring at −78° C. for 5 minutes. An aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively, dried over anhydrous sodium sulfate and concentrated to give the title compound (55.29 g) having the following physical properties.

Workup

  1. stirringby stirring at −78° C. for 5 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium hydrogen carbonate solution and brine successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-47b4e0704a144fe78f32b122a2cafea9
Source dataset
uspto-grants-2011_01
Patent number
US07875745B2

Reaction notes

Loading…