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

HRID 1680517

반응식

HRID 1680517 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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##

후처리

  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

출처 및 근거

ORD 기록
ord-5fe3e1aba09941f8a18cac19cf3012bd
출처 데이터셋
uspto-grants-1981_06
특허 번호
US04273866

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