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Sodium methanesulfinate → {3-[4-Methanesulfonyl-2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid methyl ester

HRID 885318
ノート
印刷プレビュー

反応式

HRID 885318 の反応式
[CH3:1][O:2][C:3](=[O:35])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][C:15]=2[CH2:21][N:22]2[C@@H:26]([CH3:27])[C@@H:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:24][C:23]2=[O:34])[CH:6]=1.[CH3:36][S:37]([O-:39])=[O:38].[Na+]>CN1C(=O)CCC1.[Cu](I)I>[CH3:1][O:2][C:3](=[O:35])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][C:14]2[CH:19]=[CH:18][C:17]([S:37]([CH3:36])(=[O:39])=[O:38])=[CH:16][C:15]=2[CH2:21][N:22]2[C@@H:26]([CH3:27])[C@@H:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:24][C:23]2=[O:34])[CH:6]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2733271Sodium methanesulfinateHCID 58237509{3-[4-Bromo-2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid methyl ester

生成物 1

HCID 58237649{3-[4-Methanesulfonyl-2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid methyl ester収率 97.5%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒
HCID 13387
N-methyl-2-pyrrolidone
溶媒

反応条件

温度
150 °C

実験手順

{3-[4-Bromo-2-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid methyl ester (0.1 g, 0.19 mmol), sodium methanesulfinate (0.087 g, 0.84 mmol), and copper iodide (0.159 g, 0.84 mmol) were combined in NMP (2 mL) and degassed with N2 for 10 minutes. The reaction was then stirred at 150° C. for 3 hours, until no starting material was seen by analytical tlc. The mixture was filtered through Celite and worked-up with brine and EtOAc, and the crude material was purified by silica gel chromatography to give the desired product as a colorless oil (0.1 g).

後処理

  1. customdegassed with N2 for 10 minutes
  2. filtrationThe mixture was filtered through Celite
  3. customthe crude material was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-907f8b68cf2c4c57bb5f964b65631520
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08242145B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート