Iodine → (5R)-3-(3-Fluoro-4-iodophenyl)-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one

HRID 1371824ノート

反応式

HRID 1371824 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[N:15]3)[O:10][C:9]2=[O:20])[CH:5]=[CH:6][CH:7]=1.[I:21]I>ClCCl.FC(F)(F)C([O-])=O.[Ag+]>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[N:15]3)[O:10][C:9]2=[O:20])[CH:5]=[CH:6][C:7]=1[I:21]

参加物

5

反応物 2

HCID 807Iodine2 回HCID 58778317(5R)-3-(3-Fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one2 回

生成物 1

HCID 58778315(5R)-3-(3-Fluoro-4-iodophenyl)-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one収率 42.6%

試薬・触媒・溶媒 2

HCID 76299Silver trifluoroacetate触媒2 回HCID 6344Dichloromethane溶媒

実験手順

Silver trifluoroacetate (0.52 g, 2.35 mmol) was added to a solution of (5R)-3-(3-fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (Intermediate 1, 0.50 g, 1.81 mmol) in dichloromethane (15 ml). Iodine (0.55 g, 2.17 mmol) was added over 1.5 h, and the reaction mixture was stirred overnight. After 16 h, the solids were removed by filtration and additional silver trifluoroacetate (0.38 g, 1.72 mmol) and iodine (0.27 g, 1.06 mmol) were added. After an additional 24 h, the reaction mixture was filtered. The filter cake was washed with methanol. The methanol filtrate was concentrated under vacuum to give 0.31 g of the title product.

後処理

  1. waitAfter 16 h
  2. additionwere added
  3. waitAfter an additional 24 h
  4. filtrationthe reaction mixture was filtered
  5. washThe filter cake was washed with methanol
  6. concentrationThe methanol filtrate was concentrated under vacuum

出典と根拠

ORDレコード
ord-91dd885ee02047a4b2ec7b6476cb05cc
出典データセット
uspto-grants-2007_01
特許番号
US07157482B2

反応ノート

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