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HRID258236

反应详情

EQUATION

反应方程式

HRID 258236 的结构方程式

REACTANTS

反应物

3
结构：Cc1ccc(S(=O)(=O)N(C)N=O)cc1
HCID6628

N-Methyl-N-nitrosotoluene-4-sulphonamide

C8H10N2O3S

结构：C=[N+]=[N-]
HCID9550

Diazomethane

CH2N2

结构：C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
HCID10133

Chenodeoxycholic acid

C24H40O4

PRODUCTS

生成物

1
结构：COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
HCID11069533

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CCOCC
溶剂HCID3283

Diethyl Ether

C4H10O

结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

Chenodeoxycholic acid (0.5 g, 1.3 mmol) in THF (10 ml) at 0° C. was treated dropwise with freshly prepared diazomethane in ether (prepared in the usual manner from diazald) until the yellow colour persisted. After 15 minutes at 0° C. the solvent was evaporated to yield a white foam (0.55 g). The compound would not recrystallise, although gas chromatography showed the product to be 97% pure. The product was further purified by preparative silica tlc. (solvent system: EtOAc/CH2Cl2 /AcOH--10:10:1) to afford pure methyl chenodeoxycholate3 (0.42 g, 81%) as a foam: 1H NMR (60 MHz; CDCl3) δ0.65 (3H, s, 18-CH3), 0.91 (3H, s, 19-CH3), 1.85 (2H, s [exchanges on adding D2O], 3α and 7α OH's), 3.1-3.7 (1H, m, 3β-H), 3.64 (3H, s, --OMe), 3.7-3.9 (1H, m, 7β-H); IR (nujol mull) 3384 (OH's), 1740 (C=O) cm-1 ; MS: Found m/z 406.3077; C25H42O4 (M) requires 406.3083.

WORKUP

后处理

  1. customAfter 15 minutes at 0° C. the solvent was evaporated