Methyl chloroformate → (S)-N-[[3-[3-Fluoro-4-[1-(carboxymethyl)-3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1004847ノート

反応式

HRID 1004847 の反応式
[CH2:1](N(CC)CC)C.Cl[C:9]([O:11]C)=[O:10].[F:13][C:14]1[CH:15]=[C:16]([N:24]2[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]2=[O:34])[CH:17]=[CH:18][C:19]=1[CH:20]1[CH2:23][NH:22][CH2:21]1>C(Cl)(Cl)Cl>[F:13][C:14]1[CH:15]=[C:16]([N:24]2[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]2=[O:34])[CH:17]=[CH:18][C:19]=1[CH:20]1[CH2:23][N:22]([CH2:1][C:9]([OH:11])=[O:10])[CH2:21]1

参加物

5

反応物 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 53667482(S)-N-[[3-[3-Fluoro-4-[3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

生成物 1

HCID 54000610(S)-N-[[3-[3-Fluoro-4-[1-(carboxymethyl)-3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

Triethylamine (150 μL, 1.08 mmol) and methyl chloroformate (65 μL, 0.84 mmol) were added to a chloroform (5 mL) suspension of (S)-N-[[3-[3-fluoro-4-[3-azetidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (Example 82, 153 mg, 0.50 mmol) and stirred overnight. Additional chloroform (25 mL) was added and the solution washed with water (15 mL) and brine (15 mL). Drying over magnesium sulfate, filtration, and evaporation gave a foam. Chromatography over silica gel (50 g, 40-60 μm) eluting with 1-3% methanol-chloroform gave the title compound as a white solid. FAB-HRMS: theory 366.1465 (M+1); meas. 366.1468.

後処理

  1. washthe solution washed with water (15 mL) and brine (15 mL)
  2. dry with materialDrying over magnesium sulfate, filtration, and evaporation
  3. customgave a foam
  4. washChromatography over silica gel (50 g, 40-60 μm) eluting with 1-3% methanol-chloroform

出典と根拠

ORDレコード
ord-069ac55a489c455e808b7d46a9101b3d
出典データセット
uspto-grants-2000_04
特許番号
US06051716

反応ノート

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