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

HRID 2175162ノート

反応式

HRID 2175162 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-efe654689a0d47b5a21c145335762ba2
出典データセット
uspto-grants-2015_06
特許番号
US09062056B2

反応ノート

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