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

HRID 2120079노트

반응식

HRID 2120079 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 178471938HCID 178471938, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3fa5938a705a405fb7afb29b597f0098
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06689769B2

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