4-Methylmorpholine → HCID 10309686, compound

HRID 2211690Notes

Reaction equation

HRID 2211690 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[F:14][C:15]1[CH:16]=[C:17]([N:29]2[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]2=[O:39])[CH:18]=[C:19]([F:28])[C:20]=1[CH:21]1[CH2:26][CH2:25][S:24](=[O:27])[CH2:23][CH2:22]1.CN1CCOCC1>ClCCl>[O:27]=[S:24]1(=[O:4])[CH:25]=[CH:26][CH:21]([C:20]2[C:19]([F:28])=[CH:18][C:17]([N:29]3[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]3=[O:39])=[CH:16][C:15]=2[F:14])[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 9845Trifluoroacetic anhydrideHCID 59997907HCID 59997907, compound

Product 1

HCID 10309686HCID 10309686, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (2.24 ml, 15.8 mmol) was added dropwise at room temperature to a solution of N-[[(5S)-3-[3,5-difluoro-4-(tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (2.04 g, 5.28 mmol and N-methylmorpholine (2.90 ml, 26.4 mmol) in dichloromethane (50 ml). The reaction mixture was stirred overnight at room temperature and then evaporated to dryness. The resulting crude N-({(5S)-3-[4-(3,4-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (1.95 g) was dissolved in tetrahydrofuran (100 ml) and peracetic acid (5.6 ml of a 32% solution in acetic acid, 26.4 mmol) added dropwise at 0° C. The reaction mixture was allowed to warm to room temperature, stirred overnight, and then evaporated to dryness. The residue was purified by flash column chromatography (ethyl acetate) to give white solid (1.80 g, 85%).

Workup

  1. customevaporated to dryness
  2. dissolutionThe resulting crude N-({(5S)-3-[4-(3,4-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (1.95 g) was dissolved in tetrahydrofuran (100 ml)
  3. additionperacetic acid (5.6 ml of a 32% solution in acetic acid, 26.4 mmol) added dropwise at 0° C
  4. temperatureto warm to room temperature
  5. stirringstirred overnight
  6. customevaporated to dryness
  7. customThe residue was purified by flash column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-288dae0c24064b8ebf57319b495057dc
Source dataset
uspto-grants-2006_09
Patent number
US07101874B2

Reaction notes

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