Trifluoroacetic acid → (5S)-N-[[3-[3-Fluoro-4-[1-(phenylmethyl)-3-pyrrolidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 428757ノート

反応式

HRID 428757 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])=[CH:5][C:4]=1[F:20])=[CH2:2].FC(F)(F)C(O)=O.[CH2:28]([N:35]([CH2:39][Si](C)(C)C)[CH2:36]OC)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[F:20][C:4]1[CH:5]=[C:6]([N:9]2[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])[CH:7]=[CH:8][C:3]=1[CH:1]1[CH2:2][CH2:36][N:35]([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:39]1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 53894753(S)-N-((3-(3-fluoro-4-vinylphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

生成物 1

HCID 15887434(5S)-N-[[3-[3-Fluoro-4-[1-(phenylmethyl)-3-pyrrolidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (S)-(−)-N-[[3-[4-vinyl-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (EXAMPLE 41, Step 1, 3.50 g) and trifluoroacetic acid (0.23 mL) in dry methylene chloride under N2 is treated with a solution of N-benzyl-N-(methoxymethyl) trimethylsilylmethylamine (6.10 g) in dry methylene chloride (50mL) dropwise over 4.5 hours, and the resulting solution was stirred at ambient temperature for 17 hours. The reaction mixture is then washed and saturated aqueous sodium bicarbonate (30 mL), water (30 mL) and saline (30 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue which is chromatographed on silica gel (230-400 mesh, 350 g), eluting with a gradient of methanol/methylene chloride (1/90-10/90). Pooling and concentration of those fractions with an Rf=0.19 by TLC (methanol/chloroform, 10/90) and trituration with methanol/diethyl ether gives the title compound, NMR (CDCl3, 400 MHz) 7.35, 7.25, 7.13, 6.08, 4.78, 4.03, 3.76, 3.69, 3.62, 2.97, 2.78, 2.56, 2.33, 2.02, 1.85 δ.

後処理

  1. washThe reaction mixture is then washed
  2. dry with materialsaturated aqueous sodium bicarbonate (30 mL), water (30 mL) and saline (30 mL), dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue which
  5. customis chromatographed on silica gel (230-400 mesh, 350 g)
  6. washeluting with a gradient of methanol/methylene chloride (1/90-10/90)

出典と根拠

ORDレコード
ord-178a625d766f42c5bceee34595f19094
出典データセット
uspto-grants-2001_11
特許番号
US06313307B1

反応ノート

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