Methanesulfonyl chloride → HCID 86740192, compound

HRID 371056Notes

Reaction equation

HRID 371056 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@@H:19]2[OH:23])[C@H:15]2[C@@:6]1([F:26])[C@:7]1([CH3:25])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:24])[CH:9]=[CH:8]1)(=[O:3])[CH3:2].[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1>[C:1]([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@@H:19]2[O:23][S:28]([CH3:27])(=[O:30])=[O:29])[C@H:15]2[C@@:6]1([F:26])[C@:7]1([CH3:25])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:24])[CH:9]=[CH:8]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 13421127HCID 13421127, compound

Product 1

HCID 86740192HCID 86740192, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (11β,17β)-11-(acetyloxy)-9-fluoro-17-hydroxyandrosta-1,4-dien-3-one (1.0 g; 2.9 mmole) in dry pyridine (12 ml) was stirred in an ice bath and methanesulfonyl chloride (0.435 ml; 644 mg; 5.6 mmole) was added. The solution was left standing at 0°-5° C. for 20 hours and then poured into ice-cold 20% hydrochloric acid. The mixture was extracted with chloroform, the chloroform solution was washed with water, a dilute sodium bicarbonate solution and water, dried (anhydrous magnesium sulfate) and evaporated to afford a solid (1.20 g). One crystallization from ethyl acetatehexane gave a specimen (1.0 g), melting point 210°-211° C. (dec.), with consistent spectral data.

Workup

  1. waitThe solution was left
  2. extractionThe mixture was extracted with chloroform
  3. washthe chloroform solution was washed with water
  4. dry with materiala dilute sodium bicarbonate solution and water, dried (anhydrous magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-1e05e938c9654ee9aa619a811b4dff38
Source dataset
uspto-grants-1985_07
Patent number
US04529548

Reaction notes

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