Dimethylformamide → (4R)-4-benzyl-3-[(2E)-3-(3,4-dichlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one

HRID 1260939

반응식

HRID 1260939 반응식
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C[N:15]([CH:17]=[O:18])[CH3:16].[C:19](Cl)(=[O:23])C(Cl)=O>C1COCC1>[CH2:9]([C@@H:16]1[CH2:19][O:23][C:17](=[O:18])[N:15]1[C:11](=[O:13])/[CH:10]=[CH:9]/[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 6880273,4-Dichlorocinnamic acid

생성물 1

HCID 68873145(4R)-4-benzyl-3-[(2E)-3-(3,4-dichlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one수율 49%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2E)-3-(3,4-dichlorophenyl)prop-2-enoic acid (5.0 g) and DMF (178 μL) in THF (115 mL) was added oxalyl chloride (3.98 mL) at room temperature, and the mixture was stirred for 45 min. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in THF (13.8 mL). The THF solution was added dropwise to a solution of (4R)-4-benzyl-1,3-oxazolidin-2-one (4.48 g), triethylamine (15.9 mL) and LiCl (4.87 g) in THF (115 mL) at 0° C., and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with water and brine and dried, and the solvent was evaporated under reduced pressure to give (4R)-4-benzyl-3-[(2E)-3-(3,4-dichlorophenyl)prop-2-enoyl]-1,3-oxazolidin-2-one (4.22 g, 49%) as a white powder.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in THF (13.8 mL)
  3. additionThe THF solution was added dropwise to a solution of (4R)-4-benzyl-1,3-oxazolidin-2-one (4.48 g), triethylamine (15.9 mL) and LiCl (4.87 g) in THF (115 mL) at 0° C.
  4. stirringthe mixture was stirred overnight at room temperature
  5. additionThe reaction mixture was poured into water
  6. extractionthe resultant product was extracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. customdried
  9. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-260d271a6c8d4170ae367f8900ecc734
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470816B2

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