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HRID1489905

反应详情

EQUATION

反应方程式

HRID 1489905 的结构方程式

REACTANTS

反应物

4
结构：CN(C)c1ccccn1
HCID21885

2-Dimethylaminopyridine

C7H10N2

结构：C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
HCID64971

Betulinic acid

C30H48O3

结构：CC1C(=O)OC(=O)C1C
HCID140145

2,3-Dimethylsuccinic anhydride

C6H8O3

结构：CO.ClC(Cl)Cl
HCID21584188

Chloroform methanol

C2H5Cl3O

PRODUCTS

生成物

1
结构：C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC(=O)C(C)(C)CC(=O)O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
HCID461257

未命名化合物

收率 3.1%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：c1ccncc1
溶剂HCID1049

Pyridine

C5H5N

PROCEDURE

实验过程

3-O-(2',2'-dimethylsuccinyl)betulinic acid (2) was prepared as above using a solution of betulinic acid, dimethylaminopyridine, and dimethylsuccinic anhydride in anhydrous pyridine. The yield was 3.1%. Crystallization form methanol gave colorless needles, melting point 279°-280° C.; [α]D19 +36.2° [c=0.35, CHCl3-MeOH (1:1)]; positive FABMS m/z 585 (M+H)+ ; Negative FABMS m/z 583 (M-H)- ; HR-FABMS calculated for C36H57O6 585.4155, found m/z 585.4156; 1H NMR (pyridine-d5): 0.75, 0.93, 1.03 (×2), 1.06 (each 3H, s; 4-(CH3)2, 8-CH3, 10-CH3, 14-CH3), 1.49 (6H, 2, 2'-CH3 ×2), 1.80 (3H, s, 20-CH3), 2.94 (2H, s, H2-3'), 3.55 (1H, m, H-19), 4.77 (1H, dd, J=5, 11.5 Hz, H-3), 4.79, 4.95 (each 1H, br s, H-30).

WORKUP

后处理

  1. customCrystallization
  2. customform methanol
  3. customgave colorless needles, melting point 279°-280° C.