4-Methylmorpholine → HCID 10193784, compound

HRID 1816435Notes

Reaction equation

HRID 1816435 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[O:14]=[S:15]1[CH2:20][CH2:19][CH:18]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:31][C@H:30]([CH2:32][NH:33][C:34](=[O:36])[CH3:35])[O:29][C:28]3=[O:37])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1.CN1CCOCC1>ClCCl>[O:14]=[S:15]1(=[O:4])[CH:16]=[CH:17][CH:18]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:31][C@H:30]([CH2:32][NH:33][C:34](=[O:36])[CH3:35])[O:29][C:28]3=[O:37])=[CH:23][CH:22]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 9845Trifluoroacetic anhydrideHCID 67550133HCID 67550133, compound

Product 1

HCID 10193784HCID 10193784, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (2.98 mL, 21.1 mmol) is added dropwise at room temperature to a solution of N-[[(5S)-3-[4-(tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (2.46 g, 7.02 mmol; prepared as described in International Publication WO 97/09328) and N-methylmorpholine (3.86 mL, 35.1 mmol) in dichloromethane (60 mL). The reaction mixture is stirred overnight at room temperature and then evaporated to dryness. The resulting crude N-[[(5S)-3-[4-(3,4-dihydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (2.77 g) is dissolved in tetrahydrofuran (100 mL) and peracetic acid (7.01 mL of a 32% solution in acetic acid) added dropwise at 0° C. The reaction mixture is allowed to warm to room temperature, stirred overnight, and then evaporated to dryness. The residue is purified by flash column chromatography (ethyl acetate) to give the title compound as white solid.

Workup

  1. customevaporated to dryness
  2. dissolutionThe resulting crude N-[[(5S)-3-[4-(3,4-dihydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (2.77 g) is dissolved in tetrahydrofuran (100 mL)
  3. additionperacetic acid (7.01 mL of a 32% solution in acetic acid) added dropwise at 0° C
  4. temperatureto warm to room temperature
  5. stirringstirred overnight
  6. customevaporated to dryness
  7. customThe residue is purified by flash column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b0e671cdabdd4246b2ddcabfb3d92b0e
Source dataset
uspto-grants-2005_04
Patent number
US06884813B2

Reaction notes

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