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Oxalyl chloride → 2-(2-fluoro-4-methanesulfonyl-phenylsulfanyl)-N-[3-(2-methoxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-propionamide

HRID 1802430
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HRID 1802430 반응식
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:12][C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=O.C(Cl)(=O)C(Cl)=O.[CH3:25][O:26][CH2:27][C:28]([C:31]1[CH:35]=[C:34]([NH2:36])[O:33][N:32]=1)([CH3:30])[CH3:29].C(N(CC)C(C)C)(C)C>CN(C=O)C.C(Cl)Cl.C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[S:12][C:13]([CH3:18])([CH3:17])[C:14]([NH:36][C:34]1[O:33][N:32]=[C:31]([C:28]([CH3:30])([CH3:29])[CH2:27][O:26][CH3:25])[CH:35]=1)=[O:16]
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참가 물질

9

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 534418093-(1-Methoxy-2-methylpropan-2-YL)isoxazol-5-amineHCID 592679272-(2-Fluoro-4-methanesulfonyl-phenylsulfanyl)-2-methyl-propionic acid

생성물 1

HCID 592678902-(2-fluoro-4-methanesulfonyl-phenylsulfanyl)-N-[3-(2-methoxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-propionamide수율 43%

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

Activation of 336 mg (1.15 mmol) of 2-(2-fluoro-4-methanesulfonyl-phenylsulfanyl)-2-methyl-propionic acid as its acid chloride is achieved by treatment with oxalyl chloride (0.3 mL, 3.45 mmol) and DMF (1 drop) in DCM (15 mL) at room temperature for 3 h. The solvent is removed under reduced pressure and the crude acid chloride is dissolved in toluene (5 mL) and added to a solution of 196 mg (1.15 mmol) of 3-(2-methoxy-1,1-dimethyl-ethyl)-isoxazol-5-ylamine and N,N-diisopropylethylamine (0.40 mL, 2.3 mmol) in toluene. The reaction is heated to 50° C. for 18 h. After cooling to room temperature, the reaction mixture is diluted with ethyl acetate (20 mL) and washed with 1M aqueous HCl solution (2×10 mL), water (2×10 mL), saturated aqueous NaHCO3 solution (2×10 mL), brine (10 mL). The organic layer is dried (Na2SO4), filtered and the filtrate is concentrated under reduced pressure. The residue is purified twice by column chromatography (silica, eluent: heptanes, 20-50% ethyl acetate, followed by heptanes, 10% ethyl acetate) to afford 220 mg of 2-(2-fluoro-4-methanesulfonyl-phenylsulfanyl)-N-[3-(2-methoxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-propionamide. Yield: 43%, ES-MS: m/z 445 [M+H]

후처리

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe crude acid chloride is dissolved in toluene (5 mL)
  3. temperatureAfter cooling to room temperature
  4. washwashed with 1M aqueous HCl solution (2×10 mL), water (2×10 mL), saturated aqueous NaHCO3 solution (2×10 mL), brine (10 mL)
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is purified twice by column chromatography (silica, eluent: heptanes, 20-50% ethyl acetate, followed by heptanes, 10% ethyl acetate)

출처 및 근거

ORD 기록
ord-77fab2d387144e9eb2e748f881302845
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08349871B2

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