Diazald → Methyl deoxycholate

HRID 258235

反応式

HRID 258235 の反応式
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:28])[C@@H:13]([OH:27])[CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[N+](=[CH2:31])=[N-].CC1C=CC(S(N(N=O)C)(=O)=O)=CC=1>C1COCC1.CCOCC>[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:28])[C@@H:13]([OH:27])[CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([O:7][CH3:31])=[O:6]

参加物

6

反応物 3

HCID 6628DiazaldHCID 9550DiazomethaneHCID 222528Deoxycholic Acid

生成物 1

HCID 229346Methyl deoxycholate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Deoxycholic acid (0.54 g, 1.4 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 (0.60 g). The compound would not recrystallise, although gas chromatography showed the product to be 99% pure. The product was further purified by preparative silica tlc. (solvent system: EtOAc/CH2Cl2 /AcOH--10:10:1) to afford pure methyl deoxycholate2 (0.45 g, 80%) as a foam: 1H NMR (60 MHz; CDCl3) δ0.67 (3H, s, 18-CH3), 0.92 (3H, s, 18-CH3), 2.18 (2H, s [exchanges on adding D2O], 3α and 12α OH's), 3.2-3.7 (1H, m. 3β-H), 3.65 (3 H, s, --OMe), 3.8-4-1 (1H, m, 12β-H); IR (nujol mull) 3368 (OH's), 1740 (C=O) cm-1 ; MS: Found m/z 388.2951; C25H40O3 (M-H2O) requires 388.2977.

後処理

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

出典と根拠

ORDレコード
ord-b0c15b2254654d1e958362c00ec2584b
出典データセット
uspto-grants-1993_11
特許番号
US05266566

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