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

HRID 747227노트

반응식

HRID 747227 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 76299Silver trifluoroacetate촉매HCID 6344Dichloromethane용매

실험 절차

Silver trifluoroacetate (0.52 g, 2.35 mM) 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 (0.50 g, 1.81 mM) in dichloromethane (15 mL). Iodine (0.55 g, 2.17 mM) was added over 1.5 h, and reaction mixture was stirred overnight. After 16 h, the solids were removed by filtration and additional silver trifluoroacetate (0.38 g, 1.72 mM) and iodine (0.27 g, 1.06 mM) 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.

후처리

  1. customreaction mixture
  2. waitAfter 16 h
  3. customthe solids were removed by filtration and additional silver trifluoroacetate (0.38 g, 1.72 mM) and iodine (0.27 g, 1.06 mM)
  4. additionwere added
  5. waitAfter an additional 24 h
  6. filtrationthe reaction mixture was filtered
  7. washThe filter cake was washed with methanol
  8. concentrationThe methanol filtrate was concentrated under vacuum

출처 및 근거

ORD 기록
ord-3da8fedb733f4554973d25ac8fbfc55d
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396847B2

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