1,1'-Carbonyldiimidazole → Benzyl((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate

HRID 708314ノート

反応式

HRID 708314 の反応式
[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[CH2:22][NH:23][CH2:24][CH2:25][OH:26].C1N=CN([C:38](N2C=NC=C2)=[O:39])C=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C@H:7]([CH2:22][N:23]2[CH2:24][CH2:25][O:26][C:38]2=[O:39])[C@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]1=[O:10]

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 118411328Benzyl ((2R,3S)-1-(2,4-dimethoxybenzyl)-2-(((2-hydroxyethyl)amino)methyl)-4-oxoazetidin-3-yl)carbamate

生成物 1

HCID 118411331Benzyl((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate収率 81.1%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of benzyl ((2R,3S)-1-(2,4-dimethoxybenzyl)-2-(((2-hydroxyethyl)amino)methyl)-4-oxoazetidin-3-yl)carbamate (4.47 g, 10.08 mmol) in chloroform (50 ml) was added CDI (4.90 g, 30.2 mmol). After stirring at rt for 30 min it was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 0-5%), affording the title compound (3.84 g, 81%) as a white foam. LCMS: Rt=0.76 min, m/z=470.1 (M+1).

後処理

  1. concentrationwas concentrated in vacuo
  2. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 0-5%)

出典と根拠

ORDレコード
ord-02d0b21945644ff4b1b9317e2e773f47
出典データセット
uspto-grants-2015_11
特許番号
US09174978B2

反応ノート

読み込み中…