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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 1809433
ノート
印刷プレビュー

反応式

HRID 1809433 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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]

後処理

  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)

出典と根拠

ORDレコード
ord-bcd28b4d932745488c1b3865e4f07b56
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08362039B2

反応ノート

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