Sulfuric Acid → 1-(2-Oxo-4-phenyloxazolidin-3-yl)-5-phenylpentane-1,5-dione

HRID 2300701Notes

Reaction equation

HRID 2300701 reaction equation
[C:1]([CH:9]([CH2:13][CH3:14])C(O)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](Cl)(=[O:20])C(C)(C)C.[C:22]1([CH:28]2[CH2:32][O:31][C:30](=[O:33])[NH:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.S(=O)(=O)(O)O>ClCCl.CN(C)C=O.CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[O:33]=[C:30]1[N:29]([C:15](=[O:20])[CH2:14][CH2:13][CH2:9][C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:8])[CH:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:32][O:31]1

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 62493Pivaloyl chlorideHCID 3497284-Phenyloxazolidin-2-one2×HCID 21651867alpha-Ethyl-beta-oxobenzenepropanoic acid

Product 1

HCID 183745891-(2-Oxo-4-phenyloxazolidin-3-yl)-5-phenylpentane-1,5-dione

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

10 g of benzoylbutyric acid and 12.5 ml of triethylamine are dissolved in 55 ml of dichloromethane. After 5 min at room temperature, 6.2 ml of pivaloyl chloride are added over a period of 30 min, and the mixture is stirred for 2 hours. 5.9 g of 4-phenyloxazolidin-2-one in 6 ml of dimethylformamide and 0.9 g of 4-(dimethylamino)pyridine are then added. The mixture is heated at reflux for about 7 hours (monitored by TLC). After the reaction has ended, the mixture is put into 15 ml of 2N sulfuric acid and stirred briefly, and the phases are then separated. The org. phase is washed with 5 percent strength bicarbonate solution and, after drying, concentrating and recrystallization from ethyl acetate/n-heptane, the product of molecular weight 337.4 (C20H19NO4); MS (DCl+): 338 (M+H+), is obtained. By the same route, optically active/enantiomerically enriched 2 is obtained when optically active/enantiomerically enriched 4-phenyloxazolidin-2-one is used.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for about 7 hours (monitored by TLC)
  3. stirringstirred briefly
  4. customthe phases are then separated
  5. washphase is washed with 5 percent strength bicarbonate solution
  6. customafter drying
  7. concentrationconcentrating
  8. customrecrystallization from ethyl acetate/n-heptane
  9. customMS (DCl+): 338 (M+H+), is obtained
  10. customis obtained when

Sources & evidence

ORD record
ord-54dbe60aad6e48b1a895965ec629c35c
Source dataset
uspto-grants-2002_12
Patent number
US06498156B2

Reaction notes

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