Sodium hydride → (+)-3-(3,4-Difluorophenyl)-5-oxo-morpholine-4-carboxylic acid-4-nitro-phenyl ester

HRID 1860399노트

반응식

HRID 1860399 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[NH:14][C:13](=[O:15])[CH2:12][O:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:20]>C1COCC1>[N+:28]([C:25]1[CH:24]=[CH:23][C:22]([O:21][C:19]([N:14]2[C:13](=[O:15])[CH2:12][O:11][CH2:10][CH:9]2[C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)=[O:20])=[CH:27][CH:26]=1)([O-:30])=[O:29]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 821294-Nitrophenyl chloroformateHCID 18623221HCID 18623221, 화합물

생성물 1

HCID 15550626(+)-3-(3,4-Difluorophenyl)-5-oxo-morpholine-4-carboxylic acid-4-nitro-phenyl ester수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 5-(3,4-difluoro-phenyl)-morpholin-3-one (0.34 g, 1.57 mmol) in 10 mL of THF was added NaH (0.05 g, 1.9 mmol) and the resulting solution was stirred for 30 min. It was then transferred via a syringe into a solution of 4-nitrophenyl chloroformate in 20 mL of anhydrous THF at −78° C. under argon. The resulting solution was stirred for 2 hours after which the solvent was removed and the residue was purified by column chromatography on silica gel with 1:1 hexane/CH2Cl2 followed by CH2Cl2 to obtain 3-(3,4-difluorophenyl)-5-oxo-morpholine-4-carboxylic acid-4-nitro-phenyl ester as a colorless thick oil (0.31 g, 51%).

후처리

  1. stirringThe resulting solution was stirred for 2 hours after which the solvent
  2. customwas removed
  3. customthe residue was purified by column chromatography on silica gel with 1:1 hexane/CH2Cl2

출처 및 근거

ORD 기록
ord-20c1f9364dac4068948f7f0b01240925
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531471B2

반응 노트

불러오는 중…