Diisopropylethylamine → ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate

HRID 874917노트

반응식

HRID 874917 반응식
FC(F)(F)C(O)=O.[NH2:8][CH2:9]/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13].ClC(Cl)(Cl)[C:19]([C:21]1[NH:22][CH:23]=[C:24]([I:26])[CH:25]=1)=[O:20].C(N(CC)C(C)C)(C)C>ClCCl>[I:26][C:24]1[CH:25]=[C:21]([C:19]([NH:8][CH2:9]/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:20])[NH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 116816022,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethan-1-oneHCID 72699081ethyl (2E)-4-aminobut-2-enoate trifluoroacetate

생성물 1

HCID 86658329ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate수율 68.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ethyl (2E)-4-aminobut-2-enoate trifluoroacetate (IV) (0.97 g, 4 mmol) was added to a solution of 2,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethanone (IX) (0.68 g, 2 mmol) and N,N-diisopropylethylamine (DIPEA) (2.7 mL, 16 mmol) in dichloromethane (20 mL) and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under vacuum and the residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1) to obtain compound ethyl (2E)-4-{[(4-iodo-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate (X, where R1=OCH2CH3) as an off-white solid (0.48 g, 68% yield).

후처리

  1. customThe solvent was evaporated under vacuum
  2. customthe residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1)

출처 및 근거

ORD 기록
ord-26ec8f7cbd5444fa8efa07bc7507b104
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981092B2

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