(S)-N-[3-[3-Fluoro-4-aminophenyl]-2-oxo-5-oxazolidinyl]methylacetamide → HCID 178471938, compound

HRID 2120079Notes

Reaction equation

HRID 2120079 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5](=[CH:17][N:18]([CH3:20])C)[C:6](=[O:16])[C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15])[CH3:2].[C:22]([NH:25][CH2:26][C@@H:27]1[O:31][C:30](=[O:32])[N:29]([C:33]2[CH:38]=[CH:37]C(N)=[C:35]([F:40])[CH:34]=2)[CH2:28]1)(=[O:24])[CH3:23]>CCO>[C:22]([NH:25][CH2:26][CH:27]1[O:31][C:30](=[O:32])[N:29]([C:33]2[CH:38]=[CH:37][C:20]([NH:18]/[CH:17]=[C:5](/[C:6]([C:7]3[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=3[F:15])=[O:16])\[C:4]([O:3][CH2:1][CH3:2])=[O:21])=[C:35]([F:40])[CH:34]=2)[CH2:28]1)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 10778218(S)-N-[3-[3-Fluoro-4-aminophenyl]-2-oxo-5-oxazolidinyl]methylacetamideHCID 53640509HCID 53640509, compound

Product 1

HCID 178471938HCID 178471938, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (2.09 mL, 15 mmol) was added with stirring to a solution of 2,4,5-trifluorobenzoyl chloride (1.95 g, 10 mmol) and ethyl 3-dimethylaminoacrylate 20 (1.43 g, 10 mmol) in 1,4-dioxane (20 mL). The mixture was stirred at r.t. overnight, and solvent was removed under vacuum. The residue was dissolved in ethyl ether (100 mL) and hexanes (20 mL), and the resulting mixture was washed with water (2×100 mL), 2% aq. citric acid (2×100 mL), brine (100 mL), 2.5% aq. NaHCO3 (2×100 mL), and brine (100 mL). The organic layer was dried (MgSO4), and the solvents removed under vacuum to provide ethyl-2-(dimethylamino)methylene-2-(2,4,5-trifluorobenzoyl)acetate 21 as a light orange oil (Yield 2.55 g (85%). MS (m/z): 302 [M+H]+. Rt 4.9 min.). A solution of Compound 21 (0.301 g, 1.0 mmol) and 5-(S)-acetamidomethyl-3-(4-amino-3-fluorophenyl)-oxazolidine-2-one (0.267 g, 1.0 mmol) in EtOH (9 mL) was agitated at 40° C. for 16 h. The solvent was removed under vacuum, and the resulting residue dissolved in ethyl ether (75 mL). The ether solution was washed with 3% aq. citric acid (2×40 mL), brine (40 mL), and dried (MgSO4). The solvent was removed under vacuum to afford Compound 22 as a thick light-orange oil. Yield 0.50 g (90%). MS (m/z): 524 [M+H]+. Rt 5.5 min.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe resulting residue dissolved in ethyl ether (75 mL)
  3. washThe ether solution was washed with 3% aq. citric acid (2×40 mL), brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-3fa5938a705a405fb7afb29b597f0098
Source dataset
uspto-grants-2004_02
Patent number
US06689769B2

Reaction notes

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