Acetyl chloride → 3alpha-Acetylcholanic acid

HRID 859077

反応式

HRID 859077 の反応式
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:27])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23](O)[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].C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>O1CCCC1>[C:35]([C@@H:23]1[CH2:22][CH2:21][C@@:20]2([CH3:26])[CH:19]([CH2:18][CH2:17][C@@H:16]3[C@@H:15]2[CH2:14][CH2:13][C@@:12]2([CH3:27])[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)(=[O:37])[CH3:36]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 9903Lithocholic Acid

生成物 1

HCID 183460023alpha-Acetylcholanic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To tetrahydrofuran was added 0.1 mole of lithocholic acid and 0.1 mole of triethylamine, and the resulting solution was maintained at a temperature below 4° C. in an ice bath. 0.12 mole of acetyl chloride was slowly added thereto, and the resulting solution was reacted for 8 hours. Thereafter, residual solvent was removed by using a vacuum distillator. A compound was extracted by using ethyl acetate, and washed with water a few times, to obtain 3α-acetylcholanic acid. To tetrahydrofuran was added 0.2 mole of 3α-acetylcholanic acid thus obtained and a slight amount of p-toluensulfonic acid. 0.21 mole of ethylvinylether was added to the resulting solution. Then, the resulting solution was reacted for 12 hours, to obtain 3α-acetylethoxyethyl lithocholate of formula 3 (yield: 70%).

後処理

  1. temperaturethe resulting solution was maintained at a temperature below 4° C. in an ice bath
  2. customthe resulting solution was reacted for 8 hours
  3. customThereafter, residual solvent was removed
  4. extractionA compound was extracted
  5. washwashed with water a few times

出典と根拠

ORDレコード
ord-66f90cdfab304ccfac345517ad8a44d7
出典データセット
uspto-grants-2006_12
特許番号
US07150961B2

関連ノート

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