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

HRID 1814029

反応式

HRID 1814029 の反応式
[O-]CCCC.[Li+].C([O:14][C:15](=[O:31])[NH:16][C:17]1[CH:22]=[C:21]([F:23])[C:20]([N:24]2[CH2:29][CH:28]3[CH:26]([CH2:27]3)[CH2:25]2)=[C:19]([F:30])[CH:18]=1)C1C=CC=CC=1.CO.[C:34]([NH:37][CH2:38][C@H:39](OC(=O)C)[CH2:40]Cl)(=[O:36])[CH3:35].[Cl-].[NH4+]>CN(C=O)C.[Cl-].[Na+].O.O.C1COCC1>[CH:26]12[CH2:27][CH:28]1[CH2:29][N:24]([C:20]1[C:19]([F:30])=[CH:18][C:17]([N:16]3[CH2:40][C@H:39]([CH2:38][NH:37][C:34](=[O:36])[CH3:35])[O:14][C:15]3=[O:31])=[CH:22][C:21]=1[F:23])[CH2:25]2

参加物

10

反応物 5

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 7357675(2S)-1-Acetamido-3-chloropropan-2-yl acetateHCID 11290870[4-(3-Aza-bicyclo[3.1.0]hex-3-yl)-3,5-difluoro-phenyl]-carbamic acid benzyl esterHCID 23676864Lithium butan-1-olate

生成物 1

HCID 11405435N-({(5S)-3-[4-(3-azabicyclo[3.1.0]hex-3-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl) acetamide

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Lithium butoxide solution (1.6 mL of a 1.0 M THF solution, 1.6 mmol) was added to a cooled (0° C.) solution of [4-(3-aza-bicyclo[3.1.0]hex-3-yl)-3,5-difluoro-phenyl]-carbamic acid benzyl ester (0.180 g, 0.52 mmol) in DMF (0.35 mL) and MeOH (0.042 mL, 1.05 mmol). Solid (S)-acetic acid 2-acetylamino-1-chloromethyl-ethyl ester (0.203 g, 1.05 mmol) was then added and the solution allowed to warm to room temperature and stirred for 20 h. Saturated aqueous ammonium chloride (0.8 mL) was added, along with 7 mL of H2O and 6 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 (0-2% MeOH-DCM) to provide N-({(5S)-3-[4-(3-azabicyclo[3.1.0]hex-3-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl) acetamide.

後処理

  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 (0-2% MeOH-DCM)

出典と根拠

ORDレコード
ord-1bbf5acdeb4d49e692d9f862f4995323
出典データセット
uspto-grants-2005_04
特許番号
US06875784B2

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