Hydrochloric Acid → HCID 86745915, compound

HRID 1648435Notes

Reaction equation

HRID 1648435 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[OH:5][CH2:6][C@@H:7]([CH3:28])[C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1.S(Cl)([Cl:32])(=O)=O.Cl>N1C=CC=CC=1>[C:1]([OH:4])(=[O:3])[CH3:2].[Cl:32][C:16]1[C:17](=[O:27])[CH2:18][CH2:19][C@@:20]2([CH3:21])[C:15]=1[CH2:14][CH2:13][C@@H:12]1[C@@H:22]2[CH2:23][CH2:24][C@@:25]2([CH3:26])[C@H:11]1[CH2:10][CH2:9][C@@H:8]2[C@H:7]([CH3:28])[CH2:6][OH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24648Sulfuryl chlorideHCID 86745918HCID 86745918, compound

Product 1

HCID 86745915HCID 86745915, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of (20S)-21-hydroxy-20-methylpregn-4-en-3-one acetate (10.2 g, 27.38 mmol) in pyridine (100 mL) cooled to 15° C. there was added sulfuryl chloride (4.4 mL, 54.76 mmol) dropwise. After 30 minutes, the reaction mixture was poured into 1N hydrochloric acid and extracted with ether. The combined organic extracts were successively washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine. The solution was then dried over magnesium sulfate and concentrated to give an orange solid. Flash chromatography of this material [eluting with ethyl acetate-hexane (3:7)] gave (20S)-4-chloro-21-hydroxy-20-methylpregn-4-en-3-one acetate as a white solid (8.5 g, 72%).

Workup

  1. extractionextracted with ether
  2. washThe combined organic extracts were successively washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine
  3. dry with materialThe solution was then dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give an orange solid
  6. washFlash chromatography of this material [eluting with ethyl acetate-hexane (3:7)]

Sources & evidence

ORD record
ord-594bcf2c255c453c8d049915b70cf172
Source dataset
uspto-grants-1995_07
Patent number
US05436237

Reaction notes

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