Imidazole → 3alpha-(t-Butyldimethylsilyloxy)-7alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid

HRID 1680517

反応式

HRID 1680517 の反応式
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:29])[C@@H:13]([OH:28])[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][C@@H:17]([OH:27])[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].N1C=CN=C1.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].O>CN(C)C=O>[Si:35]([O:25][C@@H:23]1[CH2:22][CH2:21][C@@:20]2([CH3:26])[C@H:19]([CH2:18][C@@H:17]([OH:27])[C@@H:16]3[C@@H:15]2[CH2:14][C@H:13]([OH:28])[C@@:12]2([CH3:29])[C@H:11]3[CH2:10][CH2:9][C@@H:8]2[C@H:2]([CH3:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])[CH2:24]1)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 221493Cholic Acid

生成物 1

HCID 704792183alpha-(t-Butyldimethylsilyloxy)-7alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Cholic acid, 4.08 g, is dissolved in 10 ml of dry dimethylformamide and 3.40 g of imidazole is added, followed by 3.60 g of t-butyldimethylsilyl chloride. The reaction mixture is allowed to stand overnight at room temperature. The reaction mixture is poured into water, filtered and the precipitate is washed with water. This precipitate is dissolved in 30 ml of tetrahydrofuran and 3 ml of water and 2 ml of acetic acid is added. After 6.5 hours, the solvent is evaporated and the residue chromatographed on 200 g of silica gel with 5% methanol in methylene chloride as eluent, to provide 3α-(t-butyldimethylsilyloxy)-7α,12α-dihydroxy-5β-cholan-24-oic acid, mp 145.5-148, having the following structural formula: ##STR14##

後処理

  1. filtrationfiltered
  2. washthe precipitate is washed with water
  3. dissolutionThis precipitate is dissolved in 30 ml of tetrahydrofuran
  4. addition3 ml of water and 2 ml of acetic acid is added
  5. waitAfter 6.5 hours
  6. customthe solvent is evaporated
  7. customthe residue chromatographed on 200 g of silica gel with 5% methanol in methylene chloride as eluent

出典と根拠

ORDレコード
ord-5fe3e1aba09941f8a18cac19cf3012bd
出典データセット
uspto-grants-1981_06
特許番号
US04273866

関連ノート

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