Methanesulfonyl chloride → HCID 86736736, compound

HRID 1448020Notes

Reaction equation

HRID 1448020 reaction equation
[OH:1][C@@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:4]([C@@H:5]([OH:30])[CH2:6][C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH2:3]1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1>[S:32]([OH:34])(=[O:1])(=[O:33])[CH3:31].[S:32]([OH:34])(=[O:1])(=[O:33])[CH3:31].[OH:1][C@@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:4]([C@@H:5]([OH:30])[CH2:6][C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH2:3]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22809505HCID 22809505, compound

Product 1

HCID 86736736HCID 86736736, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of 3α,6α-dihydroxy-5β-cholestan-24-one (168 mg) in pyridine (5 ml) was added methanesulfonyl chloride (0.5 ml) under cooling in an ice bath and the mixture was continuously stirred for one hour. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous solution of hydrochloric acid and then with water, dried over magnesium sulfate and evaporated to give an oily product, 3α,6α-dihydroxy-5β-cholestan-24-one dimesylate.

Workup

  1. temperatureunder cooling in an ice bath
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with an aqueous solution of hydrochloric acid
  4. dry with materialwith water, dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-dba2060148904e29b858a42108334d8f
Source dataset
uspto-grants-1979_12
Patent number
US04179452

Reaction notes

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