Triethylamine → Ethyl 5-(3-((tert-butoxycarbonyl)amino)phenyl)isoxazole-3-carboxylate

HRID 1375659ノート

反応式

HRID 1375659 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[CH:15])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][CH2:18][O:19][C:20](/[C:22](/Cl)=[N:23]\[OH:24])=[O:21].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C.Cl>[CH2:18]([O:19][C:20]([C:22]1[CH:15]=[C:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:16])[CH:9]=2)[O:24][N:23]=1)=[O:21])[CH3:17]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetateHCID 11275982tert-Butyl 3-ethynylphenylcarbamate

生成物 1

HCID 49775748Ethyl 5-(3-((tert-butoxycarbonyl)amino)phenyl)isoxazole-3-carboxylate収率 69.7%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(3-ethynyl-phenyl)-carbamic acid tert-butyl ester (2.48 g, 0.0114 mole) and ethyl chlorooximidoacetate (3.82 g, 0.0252 mole) were mixed in THF (12 mL) and triethylamine (3.98 mL, 0.0286 mole) was added slowly. The mixture was stirred for 16 hours and then diluted with ethyl acetate (100 mL) and aqueous 1N HCl (50 mL). The two layers were separated and the aqueous layer extracted with ethyl acetate (2×50 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated in vacuo and purified by flash chromatography (10–15% ethyl acetate/Hexane) to provide the titled compound (2.64 g, 50% yield).

後処理

  1. customThe two layers were separated
  2. extractionthe aqueous layer extracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organics were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (10–15% ethyl acetate/Hexane)

出典と根拠

ORDレコード
ord-f7cc28789b104eed8ee397c60fb8c163
出典データセット
uspto-grants-2007_01
特許番号
US07169797B2

反応ノート

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