氨 → Tert-butyl 3-sulfamoylbenzoate

HRID 132069

反应方程式

HRID 132069 反应方程式
S(=O)(=O)(O)O.[O-]S([O-])(=O)=O.[Mg+2].Cl[S:13]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([OH:21])=[O:20])(=[O:15])=[O:14].[CH3:25][C:26](O)([CH3:28])[CH3:27].[NH3:30]>C(Cl)Cl.CO>[C:26]([O:21][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][CH:24]=[C:16]([S:13](=[O:15])(=[O:14])[NH2:30])[CH:17]=1)([CH3:28])([CH3:27])[CH3:25]

参与物

8

反应物 5

HCID 222氨HCID 1118四氧化硫HCID 6386叔丁醇HCID 24083Sulfuric acid magnesium salt (1:1)HCID 776413-氯磺酰基苯甲酸

产物 1

HCID 59733695Tert-butyl 3-sulfamoylbenzoate收率 42.9%

试剂、催化剂与溶剂 2

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂HCID 6344二氯甲烷溶剂

反应条件

温度
0 °C

实验过程

Sulfuric acid (conc., 498 μL, 9.06 mmol) was added to a suspension of MgSO4 (4.36 g, 36.22 mmol) in CH2Cl2 (36 mL). The reaction mixture was stirred for 15 minutes, treated with 3-chlorosulfonyl-benzoic acid (Aldrich, 2 g, 9.06 mmol) and 2-methyl-propan-2-ol (anhydrous, 4.33 mL, 45.27 mmol), capped tightly, and stirred overnight at room temperature. The next day, the mixture was cooled to 0° C., treated with 7N NH3 in methanol (Aldrich, 40 mL) dropwise, and stirred for 30 minutes. The solvents were removed in vacuo and the crude was dissolved in ethyl acetate and saturated NaHCO3. The organic layer was washed with saturated NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as a white solid (1 g, 42.9% yield). 1H-NMR (CDCl3): δ 8.51-8.53 (m, 1H), 8.20-8.21 (m, 1H), 8.08-8.11 (m, 1H), 7.57-7.62 (m, 1H), 5.09 (bs, 2H), and 1.61 (s, 9H).

后处理

  1. customcapped tightly
  2. stirringstirred overnight at room temperature
  3. stirringstirred for 30 minutes
  4. customThe solvents were removed in vacuo
  5. dissolutionthe crude was dissolved in ethyl acetate
  6. washThe organic layer was washed with saturated NaHCO3, water, and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-14e21cc56839443387ef6672069b44f4
来源数据集
uspto-grants-2008_06
专利号
US07385066B2

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