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

HRID 1375659노트

반응식

HRID 1375659 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

(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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f7cc28789b104eed8ee397c60fb8c163
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169797B2

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