1,2-Dichloroethane → 3-(4-Hydroxy-2-{[(pyrazine-2-carbonyl)-amino]-methyl}-phenyl)-propionic acid tert-butyl ester

HRID 1181046ノート

反応式

HRID 1181046 の反応式
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:24]([O:28][C:29](=[O:41])[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][C:33]=1[CH2:39][NH2:40])([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl.O>[C:24]([O:28][C:29](=[O:41])[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][C:33]=1[CH2:39][NH:40][C:7]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9])([CH3:27])([CH3:25])[CH3:26]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 10472-Pyrazinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 17984622Tert-butyl-3-[2-(aminomethyl)-4-hydroxyphenyl]propanoate

生成物 1

HCID 589790143-(4-Hydroxy-2-{[(pyrazine-2-carbonyl)-amino]-methyl}-phenyl)-propionic acid tert-butyl ester収率 70.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of pyrazine-2-carboxylic acid (0.570 g, 4.60 mmol) in CH2Cl2 (50 mL) was added EDC (0.960 g, 5.01 mmol) and HOBt (0.620 g, 4.60 mmol) at room temperature. The mixture was stirred for 10 min, and 3-(2-aminomethyl-4-hydroxy-phenyl)-propionic acid tert-butyl ester (1.05 g, 4.18 mmol) was added. The reaction mixture was stirred for 18 h at room temperature, treated with water (50 mL), and extracted with CH2Cl2 (2×50 mL). The combined organic layers were dried (Na2SO4), concentrated, and purified by silica gel chromatography (EtOAc/hexanes, 1:1 to 1:0) to obtain the title compound (1.05 g, 70%). 1H NMR (400 MHz, CDCl3): δ 1.40 (s, 9H), 2.52 (t, 2H, J=7.6 Hz), 2.91 (t, 2H, J=7.6 Hz), 4.66 (d, 2H, J=6.4 Hz), 6.73 (dd, 1H, J=2.9, 7.8 Hz), 6.83 (d, 1H, J=2.4 Hz), 7.07 (d, 1H, J=8.3 Hz), 8.17 (br s, 1H), 8.49 (dd, 1H, J=1.5, 2.4 Hz), 8.73 (d, 1H, J=2.4 Hz), 9.41 (d, 1H, J=1.5 Hz). MS (ES) m/z 356.1 ([M−H]−).

後処理

  1. stirringThe reaction mixture was stirred for 18 h at room temperature
  2. extractionextracted with CH2Cl2 (2×50 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (EtOAc/hexanes, 1:1 to 1:0)

出典と根拠

ORDレコード
ord-f2e1111105ef463ba52fc8b52d4fe280
出典データセット
uspto-grants-2007_10
特許番号
US07282501B2

反応ノート

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