N-({(5S)-3-[4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide → N-({(5S)-3-[4-(1-methyl-2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide

HRID 10832ノート

反応式

HRID 10832 の反応式
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][CH:9]=2)=[CH:4][C:3]1=[O:25]>CO.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][CH:9]=2)[CH2:4][C:3]1=[O:25]

参加物

4

反応物 1

HCID 69557640N-({(5S)-3-[4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide

生成物 1

HCID 10246970N-({(5S)-3-[4-(1-methyl-2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide収率 97.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a mixture of N-({(5S)-3-[4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (0.170 g. 0.49 mmol) in 20 mL of MeOH is added 0.05 g of 10% palladium on activated charcoal. The mixture is hydrogenated at 50 psi for 16 hours. The reaction mixture is filtered through celite, silica is added and the mixture is concentrated to dryness. The residue is loaded onto a SIM and purified on a Biotage 12S column with 2% MeOH in CH2Cl2 to yield the desired compound (0.165 g, 96%). 1H-NMR (DMSO) δ: 8.25, 7.48, 7.28, 4.70, 4.10, 3.72, 3.40, 3.29, 3.05, 2.84, 2.39, 1.93, 1.83.

後処理

  1. filtrationThe reaction mixture is filtered through celite, silica
  2. additionis added
  3. concentrationthe mixture is concentrated to dryness
  4. custompurified on a Biotage 12S column with 2% MeOH in CH2Cl2

出典と根拠

ORDレコード
ord-aafc07e1d0ec45f3bf9d814970cd12ea
出典データセット
uspto-grants-2006_08
特許番号
US07094900B2

反応ノート

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