4-Methylmorpholine → HCID 10237397, compound

HRID 1816431Notes

Reaction equation

HRID 1816431 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. Step 2: Preparation of N-[[(5S)-3-[4-[2,3-dihydro-1,1-dioxido-6-(trifluoroacetyl)-4H-1,4-thiazin-4-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide.

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-ced94a0375cd4636896613b77a97412e
Source dataset
uspto-grants-2005_04
Patent number
US06884813B2

Reaction notes

Loading…