3-Butyn-1-OL → (R)-3-(3-fluoro-4-iodophenyl)-5-((4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one

HRID 1484702Notes

Reaction equation

HRID 1484702 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([I:17])=[C:13]([F:18])[CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3].[CH2:19]([OH:23])[CH2:20][C:21]#[CH:22].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.[O-]S([O-])(=O)=O.[Cu+2]>[F:18][C:13]1[CH:12]=[C:11]([N:7]2[CH2:6][C@H:5]([CH2:4][N:1]3[CH:22]=[C:21]([CH2:20][CH2:19][OH:23])[N:3]=[N:2]3)[O:9][C:8]2=[O:10])[CH:16]=[CH:15][C:14]=1[I:17]

Participants

6

Reactant 3

HCID 135663-Butyn-1-OLHCID 23626594(5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-oneHCID 23667548Sodium Ascorbate

Product 1

HCID 118092457(R)-3-(3-fluoro-4-iodophenyl)-5-((4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-oneYield 104.7%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

In Ar atmosphere, (R)-5-(azidomethyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one (WO 2003022824 or F. Reck, et al. J. Med. Chem. 2007, 50, 4868, 70 mg, 0.19 mmol) and but-3-yn-1-ol (27 mg, 0.38 mmol) were dissolved in t-BuOH/H2O (1 mL: 0.5 mL), added with CuSO4 (7 mg, 0.042 mmol) and Sodium ascorbate (8 mg, 0.042 mmol), and agitated at a room temperature for 1 hour. The reacting solution was concentrated under vacuum, added with H2O (5 mL) and extracted with DCM (10 mL×2). Collected organic layer was washed with brine, dried with Na2SO4, filtrated and concentrated under vacuum. The concentrated product was purified with column chromatography ((MC:MeOH:H2O:NH4OH=280:20:1:1), to obtain the subject compound (86 mg).

Workup

  1. concentrationThe reacting solution was concentrated under vacuum
  2. additionadded with H2O (5 mL)
  3. extractionextracted with DCM (10 mL×2)
  4. washCollected organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated under vacuum
  8. customThe concentrated product was purified with column chromatography ((MC:MeOH:H2O:NH4OH=280:20:1:1)

Sources & evidence

ORD record
ord-7fe7ea5e8cf6468aa769918b554b1a30
Source dataset
uspto-grants-2016_08
Patent number
US09422274B2

Reaction notes

Loading…