5(R)-(N-(2,2,2-Trichloroethyloxycarbonyl)-isoxazol-3-ylaminomethyl)-3-(4-imidazol-1-yl-3-fluorophenyl)oxazolidin-2-one → (5S)-3-(3-fluoro-4-imidazol-1-yl-phenyl)-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-one

HRID 8146

반응식

HRID 8146 반응식
ClC(Cl)(Cl)COC([N:7]([CH2:13][C@@H:14]1[O:18][C:17](=[O:19])[N:16]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH:30]=[CH:29][N:28]=[CH:27]3)=[C:22]([F:31])[CH:21]=2)[CH2:15]1)[C:8]1[CH:12]=[CH:11][O:10][N:9]=1)=O>C(O)(=O)C.O.[Zn]>[O:10]1[CH:11]=[CH:12][C:8]([NH:7][CH2:13][C@@H:14]2[O:18][C:17](=[O:19])[N:16]([C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH:30]=[CH:29][N:28]=[CH:27]4)=[C:22]([F:31])[CH:21]=3)[CH2:15]2)=[N:9]1

참가 물질

5

반응물 1

HCID 571687335(R)-(N-(2,2,2-Trichloroethyloxycarbonyl)-isoxazol-3-ylaminomethyl)-3-(4-imidazol-1-yl-3-fluorophenyl)oxazolidin-2-one

생성물 1

HCID 497417(5S)-3-(3-fluoro-4-imidazol-1-yl-phenyl)-5-[(isoxazol-3-ylamino)methyl]oxazolidin-2-one수율 41.8%

시약·촉매·용매 3

HCID 23994Zinc촉매2회HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

5(R)—(N-(2,2,2-Trichloroethyloxycarbonyl)-isoxazol-3-ylaminomethyl)-3-(4-imidazol-1-yl-3-fluorophenyl)oxazolidin-2-one (crude, 1.7 g, ˜2.5 mM), was stirred in a mixture of acetic acid (40 ml) and water (18 ml) under nitrogen at ambient temperature. Zinc dust (824 mg, 12.5 mM) was added, the mixture stirred 20 minutes, a further portion (200 mg) of zinc added, and stirring continued for 1 hour. The mixture was filtered through celite, and the filter pad washed well with a mixture of acetic acid and water (5:1). The filtrates were evaporated, and the residue partitioned between hydrochloric acid (0.5M, 200 ml) and dichloromethane (150 ml). The aqueous phase was washed with dichloromethane (100 ml), then made basic with the minimum quantity of concentrated ammonia solution, re-extracted with dichloromethane (2×150 ml), dried (magnesium sulfate), and evaporated. Recrystallisation from isopropanol (40 ml) gave the desired product (470 mg).

후처리

  1. stirringstirring
  2. waitcontinued for 1 hour
  3. filtrationThe mixture was filtered through celite
  4. washthe filter pad washed well with a mixture of acetic acid and water (5:1)
  5. customThe filtrates were evaporated
  6. customthe residue partitioned between hydrochloric acid (0.5M, 200 ml) and dichloromethane (150 ml)
  7. washThe aqueous phase was washed with dichloromethane (100 ml)
  8. extractionre-extracted with dichloromethane (2×150 ml)
  9. dry with materialdried (magnesium sulfate)
  10. customevaporated
  11. customRecrystallisation from isopropanol (40 ml)

출처 및 근거

ORD 기록
ord-0b8013c42c714262b5beb18cb83eabd9
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087629B2

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