氮 → HCID 59819846，化合物

HRID 383604

反应方程式

HRID 383604 反应方程式
N#N.[CH3:3][O:4][C:5](=[O:36])[CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:35])[CH2:21][CH2:22][C:23]2[CH:28]=[C:27]([O:29]C)[C:26]([O:31]C)=[C:25]([O:33]C)[CH:24]=2)[CH:10]=[CH:11][CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:3][O:4][C:5](=[O:36])[CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:35])[CH2:21][CH2:22][C:23]2[CH:24]=[C:25]([OH:33])[C:26]([OH:31])=[C:27]([OH:29])[CH:28]=2)[CH:10]=[CH:11][CH:12]=1

参与物

5

反应物 3

HCID 947氮HCID 25134三溴化硼HCID 16116560{2'-[3-(3,4,5-Trimethoxy-phenyl)-propionylamino]-biphenyl-3-yl}-acetic acid methyl ester

产物 1

HCID 59819846HCID 59819846，化合物收率 5%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

反应条件

温度
-78 °C

实验过程

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve {2′-[3-(3,4,5-Trimethoxy-phenyl)-propionylamino]-biphenyl-3-yl}-acetic acid methyl ester (72) (46 mg, 0.10 mmol) in anhydrous DCM (1.0 mL), cool the solution to −78° C. and add dropwise BBr3 (85 μL, 0.90 mmol). Stir the reaction mixture for 30 min at −78° C. and after slowly warming up for additional 2 h at rt. Add dropwise ice water, separate layers and extract aqu. layer with DCM (3 times). Wash combined organic layer with brine and dry with Na2SO4. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain {2′-[3-(3,4,5-Trihydroxy-phenyl)-propionylamino]-biphenyl-3-yl}-acetic acid methyl ester (73) (2 mg, 5%). 1H NMR (400 MHz, CD3CN): 2.43 (t, 2H, J=7.6 Hz); 2.69 (t, 2H, J=7.6 Hz); 3.66 (s, 3H); 3.70 (s, 2H); 6.25 (s, 2H); 7.18-7.34 (m, 5 H); 7.35-7.44 (m, 2H); 7.65 (br.s, 1H); 7.89 (br.d, 1H, J=8.3 Hz).

后处理

  1. custom(The following reaction
  2. temperatureafter slowly warming up for additional 2 h at rt
  3. customseparate layers
  4. extractionextract aqu
  5. washWash
  6. dry with materialdry with Na2SO4
  7. customPurify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95)

来源与证据

ORD记录
ord-a9dcd5bfeff7454cb3cd57ea2b25269b
来源数据集
uspto-grants-2013_02
专利号
US08367677B2

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