Diisopropylethylamine → (S)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-hexanoic acid ethyl ester

HRID 2175162노트

반응식

HRID 2175162 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1.[CH2:12]([O:14][C:15](=[O:22])[CH2:16][C@@H:17]([NH2:21])[CH2:18][CH2:19][CH3:20])[CH3:13].C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:12]([O:14][C:15](=[O:22])[CH2:16][C@@H:17]([NH:21][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1)[CH2:18][CH2:19][CH3:20])[CH3:13]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 12682302-Chloro-6-methyl-3-nitropyridineHCID 10773249Ethyl (3S)-3-aminohexanoate

생성물 1

HCID 58497448(S)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-hexanoic acid ethyl ester수율 42%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-chloro-3-nitro-6-picoline (500 mg, 2.99 mmol) in DMF (3 mL) were added the (S)-3-amino-hexanoic acid ethyl ester (554 mg, 3.48 mmol) and diisopropylethyl amine (DIPEA) (1.0 mL, 5.80 mmol). The reaction mixture was stirred at room temperature for 48 hours. The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was then dried over Na2SO4 and concentrated. The resulting residue was purified by preparative TLC using hexane and ethyl acetate (4:1) as an eluent to afford 358 mg (42%) of the title compound as orange oil. LCMS, M++1, m/z: 296.65.

후처리

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by preparative TLC

출처 및 근거

ORD 기록
ord-efe654689a0d47b5a21c145335762ba2
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062056B2

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