HCID 57126803, compound → HCID 69979965, compound

HRID 1167456Notes

Reaction equation

HRID 1167456 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][O:23][C:24]5[CH:28]=[CH:27][O:26][N:25]=5)[O:19][C:18]4=[O:29])=[CH:13][C:12]=3[F:30])[CH2:7][CH2:6]2)[O:4]CC1>C(O)(=O)C.O>[O:4]=[C:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][C@H:20]([CH2:22][O:23][C:24]4[CH:28]=[CH:27][O:26][N:25]=4)[O:19][C:18]3=[O:29])=[CH:13][C:12]=2[F:30])[CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 57126803HCID 57126803, compound

Product 1

HCID 69979965HCID 69979965, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-(4-(1,4-Dioxa-8-azaspiro[4,5]decan-8-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (3.58 g, 8.52 mmol) was dissolved in a mixture of glacial acetic acid (50 ml) and water (50 ml), and heated at 50° for 12 hours. Solvent was evaporated, the residue azeotroped with toluene (50 ml), then partitioned between EtOAc (150 ml) and water (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution (2×100 ml), water (100 ml), dried (magnesium sulfate) and evaporated. The residue was purified by chromatography on a 90 g silica Biotage column eluting with a gradient from 5:1 EtOAc to isohexane to EtOAc. Relevant fractions were combined to give the desired product (2.84 g).

Workup

  1. temperatureheated at 50° for 12 hours
  2. customSolvent was evaporated
  3. customthe residue azeotroped with toluene (50 ml)
  4. custompartitioned between EtOAc (150 ml) and water (100 ml)
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (2×100 ml), water (100 ml)
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated
  8. customThe residue was purified by chromatography on a 90 g silica Biotage column
  9. washeluting with a gradient from 5:1 EtOAc to isohexane to EtOAc

Sources & evidence

ORD record
ord-2f63e96cb7034c2dab2d91ae152f1563
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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