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

HRID 1452569ノート

反応式

HRID 1452569 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 14) (0.50 g, 1.81 mmol) in dichloromethane (15 ml). Iodine (0.55 g, 2.17 mmol) was added over 1.5 hours, and it was stirred overnight. After 16 hours, 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 and additional 24 hours, 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 hours
  2. additionwere added
  3. filtrationAfter and additional 24 hours, the reaction mixture was filtered
  4. washThe filter cake was washed with methanol
  5. concentrationThe methanol filtrate was concentrated under vacuum

出典と根拠

ORDレコード
ord-5d4b024d1ec34ecbba76904b9c21b5c8
出典データセット
uspto-grants-2009_01
特許番号
US07473699B2

反応ノート

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