4-Toluenesulfonyl chloride → HCID 86746923, 화합물

HRID 1587034노트

반응식

HRID 1587034 반응식
[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

참가 물질

7

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 67857083HCID 67857083, 화합물

생성물 1

HCID 86746923HCID 86746923, 화합물

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 21584119Ethylacetate methanol용매HCID 21877088Acetonitrile methylene chloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c443b81df01f4e28b3a7a1b1f329a67d
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05216015

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