(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one → 1-{[(5R)-3-(3-Fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}-1H-1,2,3-triazole-4-carbaldehyde

HRID 1782093Notes

Reaction equation

HRID 1782093 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH2:20][OH:21])[N:17]=[N:16]3)[O:11][C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[I:8]>O1CCOCC1.[O-2].[Mn+2]>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH:20]=[O:21])[N:17]=[N:16]3)[O:11][C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[I:8]

Participants

4

Reactant 1

HCID 58822464(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

Product 1

HCID 575882941-{[(5R)-3-(3-Fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}-1H-1,2,3-triazole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one (5.7 g, 13.6 mmol) and manganese oxide (3.56 g, 40.9 mmol) were mixed and heated up to 100° C. in dry 1,4-dioxane for 48 hours, then the mixture was cooled down to 70° C. and filtered through celite. The filtrate was concentrated and dissolved in 5% methanol in dichloromethane, hexaneses was added and the formed precipitates were filtered and collected as the title compound (3.6 g).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated
  3. dissolutiondissolved in 5% methanol in dichloromethane
  4. additionhexaneses was added
  5. customthe formed precipitates
  6. filtrationwere filtered
  7. customcollected as the title compound (3.6 g)

Sources & evidence

ORD record
ord-5f65c6596ddf4a568c66f998d56c951f
Source dataset
uspto-grants-2009_03
Patent number
US07498350B2

Reaction notes

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