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HRID1589956

反应详情

EQUATION

反应方程式

HRID 1589956 的结构方程式

REACTANTS

反应物

4
结构：C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO
HCID5743

Dexamethasone

C22H29FO5

结构：C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
HCID5754

Hydrocortisone

C21H30O5

结构：C[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
HCID5755

Prednisolone

C21H28O5

结构：[O-][Cl+3]([O-])([O-])O
HCID24247

Perchloric acid

HClO4

PRODUCTS

生成物

2
结构：C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
HCID5754

Hydrocortisone

C21H30O5

结构：CCC(C=O)C(=O)OC
HCID15570303

Methyl 2-formylbutanoate

C6H10O3

AUXILIARIES

试剂、催化剂与溶剂

1
结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

Hydrocortisone or prednisolone or dexamethasone or bethamethasone is reacted with an alkyl formylalkanoate in a solution of dichloromethane in the presence of catalytic amount of perchloric acid to produce the corresponding 17,21-carboxycyclic acetal pregnane derivatives, e.g., when hydrocortisone and methyl formylbutyrate are used the product is (IV) 11β-hydroxy-3,20-dioxo-17,21-(methoxycarbonyl-n-propyl) methylenedioxy-4-pregnene; when prednisolone and methyl formylacetate are used the product is (V) 11β-hydroxy-3,20-dioxo-17,21-(methoxycarbonylmethyl)methylenedioxy-1,4-pregnadiene.