Iodine → (R)-3-((3S,5R)-5-(2,4-di fluorophenyl)-5-(iodomethyl)tetrahydrofuran-3-carbonyl)-4-phenyloxazolidin-2-one

HRID 512804Notes

Reaction equation

HRID 512804 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH2:28])[CH2:10][C@@H:11]([CH2:26][OH:27])[C:12]([N:14]1[C@H:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][O:16][C:15]1=[O:25])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].[I:35]I>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([CH2:28][I:35])[O:27][CH2:26][C@@H:11]([C:12]([N:14]2[C@H:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][O:16][C:15]2=[O:25])=[O:13])[CH2:10]1

Participants

5

Reactant 3

HCID 807IodineHCID 10340Sodium CarbonateHCID 89463443(R)-3-((S)-4-(2,4-difluoro phenyl)-2-(hydroxymethyl)pent-4-enoyl)-4-phenyloxazolidin-2-one

Product 1

HCID 71534792(R)-3-((3S,5R)-5-(2,4-di fluorophenyl)-5-(iodomethyl)tetrahydrofuran-3-carbonyl)-4-phenyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To the above obtained dichloromethane layer containing (R)-3-((S)-4-(2,4-difluoro phenyl)-2-(hydroxymethyl)pent-4-enoyl)-4-phenyloxazolidin-2-one compound of formula-5, added sodium carbonate (59.4 g) followed by iodine (177.8 g) and the reaction mixture was stirred for 3 hours at 25-35° C. After completion of the reaction, the reaction mixture was quenched with 30% hypo solution and the reaction mixture was extracted with methyl tertiary butyl ether. Both organic and aqueous layers were separated and the organic layer was washed with 30% hypo solution, followed by 10% sodium chloride solution. Distilled off the solvent completely from the organic layer. Isopropanol (600 ml) was added to the obtained compound and the reaction mixture was stirred for 1½ hour at 25-30° C. Filtered the solid, washed with isopropyl alcohol and then dried to get the title compound. Yield: 65 g; Chiral purity: 99.5%

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was quenched with 30% hypo solution
  3. extractionthe reaction mixture was extracted with methyl tertiary butyl ether
  4. customBoth organic and aqueous layers were separated
  5. washthe organic layer was washed with 30% hypo solution
  6. distillationDistilled off the solvent completely from the organic layer
  7. additionIsopropanol (600 ml) was added to the obtained compound
  8. stirringthe reaction mixture was stirred for 1½ hour at 25-30° C
  9. filtrationFiltered the solid
  10. washwashed with isopropyl alcohol
  11. customdried

Sources & evidence

ORD record
ord-80d7ae36f0244039bd3234a2f6e343e7
Source dataset
uspto-grants-2015_08
Patent number
US09102664B2

Reaction notes

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