4-Methylmorpholine → HCID 10237397, compound

HRID 2211680Notes

Reaction equation

HRID 2211680 reaction equation
CN1CC[O:5]CC1.[F:8][C:9]1[CH:10]=[C:11]([N:22]2[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]2=[O:32])[CH:12]=[CH:13][C:14]=1[N:15]1[CH2:20][CH2:19][S:18](=[O:21])[CH2:17][CH2:16]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[O:21]=[S:18]1(=[O:5])[CH:17]=[CH:16][N:15]([C:14]2[CH:13]=[CH:12][C:11]([N:22]3[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]3=[O:32])=[CH:10][C:9]=2[F:8])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 9845Trifluoroacetic anhydrideHCID 465952Acetamide, N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-

Product 1

HCID 10237397HCID 10237397, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methylmorpholine (1.2 mL, 11.1 mmol) is added to a solution of N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (0.690 g, 1.87 mmol; prepared as described in U.S. Pat. No. 5,688,792) in DCM (40 mL), followed by trifluoroacetic anhydride (1.06 mL, 7.5 mmol). The solution is stirred at r.t. for about 20 h, and is concentrated under vacuum, then dissolved in 100 mL of EtOAc—2.5% aq. NaHCO3 (1:1). Aqueous phase is extracted with EtOAc (2×50 mL). The combined organic layers are washed with brine, and dried (MgSO4). Solvent is removed under vacuum to afford the title compound that is used directly without further purification.

Workup

  1. customprepared
  2. concentrationis concentrated under vacuum
  3. dissolutiondissolved in 100 mL of EtOAc—2.5% aq. NaHCO3 (1:1)
  4. extractionAqueous phase is extracted with EtOAc (2×50 mL)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (MgSO4)
  7. customSolvent is removed under vacuum

Sources & evidence

ORD record
ord-651cb52fe8334c2493ce41f7f3891be7
Source dataset
uspto-grants-2006_09
Patent number
US07101874B2

Reaction notes

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