4-Toluenesulfonyl chloride → HCID 86746923、化合物

HRID 1587034ノート

反応式

HRID 1587034 の反応式
[OH:1][C@@H:2]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@H:4]([CH2:5][CH2:6][C:7]3[C@@H:21]2[CH2:20][C@H:19]([OH:26])[C@@:18]2([CH3:27])[C:8]=3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:17])[CH2:13][CH2:14][CH2:15][OH:16])[CH2:3]1.C(N(CC)CC)C.[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>C(Cl)Cl.C(#N)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CO>[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41]([O:16][CH2:15][CH2:14][CH2:13][C@H:12]([C@@H:11]2[C@:18]3([CH3:27])[C:8](=[C:7]4[C@H:21]([CH2:20][C@@H:19]3[OH:26])[C@:22]3([CH3:25])[C@@H:4]([CH2:3][C@H:2]([OH:1])[CH2:24][CH2:23]3)[CH2:5][CH2:6]4)[CH2:9][CH2:10]2)[CH3:17])(=[O:43])=[O:42])=[CH:37][CH:36]=1

参加物

7

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 67857083HCID 67857083、化合物

生成物 1

HCID 86746923HCID 86746923、化合物

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 21584119Ethylacetate methanol溶媒HCID 21877088Acetonitrile methylene chloride溶媒

実験手順

A solution of 3α, 12α-dihydroxy-5β-chol-8(14)-en-24-ol (12.8 g) in methylene chloride/acetonitrile (1:1) (180 ml) is cooled to -5° C. Triethylamine (6 ml), 4-dimethylaminopyridine (0.435 g), and p-toluenesulfonyl chloride (6.65 g) are added and the solution stirred at 0° to 4° C. for about 18 hours. The solution is diluted with ethyl acetate/methanol (9:1), washed with brine and the organic solution dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography in ether, followed by 10% methanol in ethyl acetate to give the desired product.

後処理

  1. washwashed with brine
  2. dry with materialthe organic solution dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography in ether

出典と根拠

ORDレコード
ord-c443b81df01f4e28b3a7a1b1f329a67d
出典データセット
uspto-grants-1993_06
特許番号
US05216015

反応ノート

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