4-Toluenesulfonyl chloride → HCID 86746923, compound

HRID 1587034Notes

Reaction equation

HRID 1587034 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 86746923HCID 86746923, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21584119Ethylacetate methanolSolventHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c443b81df01f4e28b3a7a1b1f329a67d
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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