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HRID522390

反应详情

EQUATION

反应方程式

HRID 522390 的结构方程式

REACTANTS

反应物

2
结构：CC(C)N=C=O
HCID61277

Propane, 2-isocyanato-

C4H7NO

结构：C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@H](C1CCCC1)NC(=O)O[C@@H]1CCC[C@H]1CC/C=C/Cc1c(nc3ccccc3c1O)O2)C(=O)NS(=O)(=O)C1CC1
HCID178455696

未命名化合物

PRODUCTS

生成物

1
结构：C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@H](C1CCCC1)NC(=O)O[C@@H]1CCC[C@H]1CC/C=C/Cc1c(nc3ccccc3c1OC(=O)NC(C)C)O2)C(=O)NS(=O)(=O)C1CC1
HCID117599051

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

4
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

结构：O
溶剂HCID962

Water

H2O

结构：CC(Cl)Cl
溶剂HCID6365

1,1-Dichloroethane

C2H4Cl2

结构：CCOC(C)=O
溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度
50 °C

PROCEDURE

实验过程

To a solution of (3aR,7S,10S,12R,21E,24aS)-7-cyclopentyl-N-{(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethenylcyclopropyl}-19-hydroxy-5,8-dioxo-1,2,3,3a,5,6,7,8,11,12,20,23,24,24a-tetradecahydro-10H-9,12-methanocyclopenta[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-10-carboxamide (Example 17) (30 mg) in dichloroethane (0.6 mL) was added isopropylisocyanate (0.037 mL) then DMAP (4.6 mg). The reaction mixture was heated to 50° C. for 1 hour. After cooling back to room temperature, the mixture was diluted with ethyl acetate and water was added. The mixture was extracted with ethyl acetate (3×). The combined organics were dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase HPLC (40% ACN-100% ACN/0.05% TFA/water) yielded 27 mg of the desired product after workup with NaHCO3 and ethyl acetate. HRMS (ES+) m/z 875.3981 (M+H)+.

WORKUP

后处理

  1. temperatureAfter cooling back to room temperature
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate (3×)
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by reverse phase HPLC (40% ACN-100% ACN/0.05% TFA/water)