Triethylamine → HCID 69982214, compound

HRID 1167478Notes

Reaction equation

HRID 1167478 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][O:19][C:20]4[CH:24]=[CH:23][O:22][N:21]=4)[O:15][C:14]3=[O:25])=[CH:9][C:8]=2[F:26])[CH2:3]1.C(N(CC)CC)C>CS(C)=O.O>[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][O:19][C:20]4[CH:24]=[CH:23][O:22][N:21]=4)[O:15][C:14]3=[O:25])=[CH:9][C:8]=2[F:26])[CH2:3]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 69980407HCID 69980407, compound

Product 1

HCID 69982214HCID 69982214, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

3-(4-((3R)-3-Hydroxy-1-pyrrolidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)-oxazolidin-2-one (700 mg, 1.9 mmol) was dissolved in DMSO(5 ml) under nitrogen and triethylamine (2.03 g, 20 mmol) added. A solution of sulfur trioxide pyridine complex (0.95 g, 6 mmol) in DMSO(5 ml) was added dropwise over 20 minutes. After stirring 1 hour at ambient temperature, the mixture was diluted with water (100 ml) and extracted into EtOAc (150 ml). The organics were washed with water (2×50 ml), brine (50 ml) and dried (magnesium sulfate). After evaporation, the residue was purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 3% MeOH in dichloromethane. Relevant fractions were combined and evaporated, and the residue crystallised from ethanol (35 ml) to give product (176 mg). MS (ESP): 362 (MH+) for C17H16FN3O5.

Workup

  1. extractionextracted into EtOAc (150 ml)
  2. washThe organics were washed with water (2×50 ml), brine (50 ml)
  3. dry with materialdried (magnesium sulfate)
  4. customAfter evaporation
  5. customthe residue was purified by chromatography on a 20 g silica Mega Bond Elut® column
  6. washeluting with
  7. temperaturea gradient increasing in polarity from 0 to 3% MeOH in dichloromethane
  8. customevaporated
  9. customthe residue crystallised from ethanol (35 ml)

Sources & evidence

ORD record
ord-6b4081e473b948ff8f7ad00791ef685f
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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