Tetrahydrofuran → (R)-5-((1H-1,2,3-Triazol-1-yl)methyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one

HRID 1949197Notes

Reaction equation

HRID 1949197 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]([Si](C)(C)C)[N:17]=[N:16]3)[O:11][C:10]2=[O:24])[CH:5]=[CH:6][C:7]=1[I:8].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][C:10]2=[O:24])[CH:5]=[CH:6][C:7]=1[I:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 59488880HCID 59488880, compound

Product 1

HCID 11257720(R)-5-((1H-1,2,3-Triazol-1-yl)methyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-oneYield 93.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the crude (5R)-3-(3-fluoro-4-iodo-phenyl)-5-(4-trimethylsilanyl-[1,2,3]triazol-1-ylmethyl)-oxazolidin-2-one (1024, 14.72 g, 32.0 mmol) in an 1 M solution of tetrabutylammonium fluoride in THF (TBAF, 128 mL, 128 mmol, 4.0 equiv) was treated with acetic acid (HOAc, 5 mL) at room temperature, and the resulting reaction mixture was stirred at room temperature for 24 h. When TLC and HPLC/MS showed that the reaction was complete, the solvents were removed in vacuo. The residue was treated with H2O (300 mL) at room temperature and the resulting mixture was stirred at room temperature for 1 h. The solids were collected by filtration, washed with H2O (2×100 mL) and 20% EtOAc/hexane (2×100 mL), dried in vacuo. The crude, (5R)-3-(3-fluoro-4-iodo-phenyl)-5-[1,2,3]triazol-1-ylmethyl-oxazolidin-2-one (1025, 11.65 g, 12.416 g theoretical, 93.8%) was obtained as off-white powders, which by HPLC/MS and 1H NMR was found to be essentially pure and was directly used in the subsequent reactions without further purification. For 1025: 1H NMR (300 MHz, DMSO-d6) 3.89 (dd, 1H, J=6.4, 9.2 Hz), 4.23 (t, 1H, J=5.4 Hz), 4.84 (d, 2H, J=4.9 Hz), 5.12-5.18 (m, 1H), 7.14 (dd, 1H, J=2.4, 8.7 Hz), 7.49 (dd, 1H, J=2.4, 8.7 Hz), 7.76 (d, 1H, J=1.0 Hz, triazole-H), 7.82 (dd, 1H, J=7.5, 8.7 Hz), 8.17 (d, 1H, J=1.0 Hz, triazole-H); C12H10FIN4O2, LCMS (EI) m/e 389 (M++H).

Workup

  1. customthe resulting reaction mixture
  2. customthe solvents were removed in vacuo
  3. additionThe residue was treated with H2O (300 mL) at room temperature
  4. stirringthe resulting mixture was stirred at room temperature for 1 h
  5. filtrationThe solids were collected by filtration
  6. washwashed with H2O (2×100 mL) and 20% EtOAc/hexane (2×100 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3392a47c280f4a759d74b9b06c35c508
Source dataset
uspto-grants-2013_03
Patent number
US08399660B2

Reaction notes

Loading…