Lawesson's reagent → (5R)-3-(3,4-dihydro-4-methyl-3-thioxo-2H-1,4-benzothiazin-7-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester

HRID 723918ノート

反応式

HRID 723918 の反応式
[CH3:1][O:2][C:3]([C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:22]=[CH:21][C:14]3[N:15]([CH3:20])[C:16](=O)[CH2:17][S:18][C:13]=3[CH:12]=2)[CH2:6]1)=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>O1CCOCC1>[CH3:1][O:2][C:3]([C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:22]=[CH:21][C:14]3[N:15]([CH3:20])[C:16](=[S:32])[CH2:17][S:18][C:13]=3[CH:12]=2)[CH2:6]1)=[O:4]

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 68489755(5R)-3-(3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzothiazin-7-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester

生成物 1

HCID 86591301(5R)-3-(3,4-dihydro-4-methyl-3-thioxo-2H-1,4-benzothiazin-7-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester収率 89.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a stirred suspension of the (5R)-3-(3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzothiazin-7-yl)-2-oxo-5-oxazolidinecarboxylic acid methyl ester (EXAMPLE 62, Step 5, 1.26 g, 3.907 mmol) in dry dioxane (25 mL) is added Lawesson's reagent (2.37 g, 5.861 mmol). This reaction mixture is heated at 70–80° C. for 1.5–2 h at which time the reaction is cooled to room temperature and concentrated under reduced pressure. The residue is washed with EtOAc (15 mL×3), sonicated and filtered to give the title compound as a yellow solid (1.18 g, 89%), MS (m/z): 339.5 [M+H]+.

後処理

  1. temperatureThis reaction mixture is heated at 70–80° C. for 1.5–2 h at which time the reaction
  2. concentrationconcentrated under reduced pressure
  3. washThe residue is washed with EtOAc (15 mL×3)
  4. customsonicated
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-e46516cb522a4274884d518e16dfc22d
出典データセット
uspto-grants-2006_11
特許番号
US07141588B2

反応ノート

読み込み中…