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

HRID 1181046노트

반응식

HRID 1181046 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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]−).

후처리

  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)

출처 및 근거

ORD 기록
ord-f2e1111105ef463ba52fc8b52d4fe280
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282501B2

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