Triethylamine → HCID 53640509, compound

HRID 2120078Notes

Reaction equation

HRID 2120078 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:17]=[C:16]([F:18])[C:15]([F:19])=[CH:14][C:10]=1[C:11](Cl)=[O:12].[CH3:20][N:21]([CH3:29])[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>O1CCOCC1>[CH2:27]([O:26][C:24](=[O:25])[C:23](=[CH:22][N:21]([CH3:29])[CH3:20])[C:11](=[O:12])[C:10]1[CH:14]=[C:15]([F:19])[C:16]([F:18])=[CH:17][C:9]=1[F:8])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 1451642,4,5-Trifluorobenzoyl chloride

Product 1

HCID 53640509HCID 53640509, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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. customsolvent was removed under vacuum
  2. dissolutionThe residue was dissolved in ethyl ether (100 mL)
  3. washhexanes (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)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-bf7930fcad1d43158da89fa402002de3
Source dataset
uspto-grants-2004_02
Patent number
US06689769B2

Reaction notes

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