Methanol → N-({(5S)-3-[4-(3-azabicyclo[3.1.0]hex-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl) acetamide

HRID 1814032

반응식

HRID 1814032 반응식
[O-]CCCC.[Li+].[CH2:7]([O:14][C:15](=[O:30])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH:27]3[CH:25]([CH2:26]3)[CH2:24]2)=[C:19]([F:29])[CH:18]=1)[C:8]1C=CC=CC=1.CO.[C:33]([NH:36][CH2:37][C@H](OC(=O)C)CCl)(=[O:35])[CH3:34].[Cl-].[NH4+]>CN(C=O)C.[Cl-].[Na+].O.O.C1COCC1>[CH:27]12[CH2:26][CH:25]1[CH2:24][N:23]([C:20]1[CH:21]=[CH:22][C:17]([N:16]3[CH2:8][C@H:7]([CH2:37][NH:36][C:33](=[O:35])[CH3:34])[O:14][C:15]3=[O:30])=[CH:18][C:19]=1[F:29])[CH2:28]2

참가 물질

10

반응물 5

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 7357675(2S)-1-Acetamido-3-chloropropan-2-yl acetateHCID 11232635[4-(3-Aza-bicyclo[3.1.0]hex-3-yl)-3-fluoro-phenyl]-carbamic acid benzyl esterHCID 23676864Lithium butan-1-olate

생성물 1

HCID 11290525N-({(5S)-3-[4-(3-azabicyclo[3.1.0]hex-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl) acetamide

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

Lithium butoxide solution (2.5 mL of a 1.0 M THF solution, 2.5 mmol) was added to a cooled (0° C.) solution of [4-(3-aza-bicyclo[3.1.0]hex-3-yl)-3-fluoro-phenyl]-carbamic acid benzyl ester (0.267 g, 0.82 mmol) in DMF (0.6 mL) and MeOH (0.060 mL, 1.64 mmol). Solid (S)-acetic acid 2-acetylamino-1-chloromethyl-ethyl ester (0.316 g, 1.64 mmol) was then added and the solution allowed to warm to room temperature and stirred for 20 h. Saturated aqueous ammonium chloride (1.0 mL) was added, along with 9 mL of H2O and 8 mL of brine. The solution was extracted with three portions of dichloromethane and the combined organic phases dried (MgSO4), filtered and concentrated. The crude product was purified by column chromatography (0-3% MeOH-DCM) to provide N-({(5S)-3-[4-(3-azabicyclo[3.1.0]hex-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl) acetamide.

후처리

  1. extractionThe solution was extracted with three portions of dichloromethane
  2. dry with materialthe combined organic phases dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (0-3% MeOH-DCM)

출처 및 근거

ORD 기록
ord-6bfc18fc535341e88e7b899c30916ae8
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875784B2

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