Hydrochloric Acid → HCID 86733744, compound

HRID 918379Notes

Reaction equation

HRID 918379 reaction equation
[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([O:26][CH2:27][CH2:28][OH:29])[C@:15]3([OH:25])[C:16](=[O:19])[CH2:17][OH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:31])[CH2:4][CH2:5][C:6](=[O:30])[CH:7]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34].Cl>N1C=CC=CC=1>[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([O:26][CH2:27][CH2:28][O:29][S:33]([CH3:32])(=[O:35])=[O:34])[C@:15]3([OH:25])[C:16](=[O:19])[CH2:17][OH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:31])[CH2:4][CH2:5][C:6](=[O:30])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 68128669HCID 68128669, compound

Product 1

HCID 86733744HCID 86733744, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 0.80 g of 9-fluoro-16α-(2-hydroxyethoxy)-11β,17,21-trihydroxypregn-4-ene-3,20-dione, 21-acetate in 10 ml of pyridine is stirred with 0.5 ml of methanesulfonyl chloride for 90 minutes at 0°C under nitrogen. The solution is poured into cold 5% hydrochloric acid and extracted with chloroform. The chloroform extract is dried and evaporated to give an oil which is chromatographed on a 20 g -- silica gel column. Elution with chloroform gives 521 mg of TLC pure 9-fluoro-16α-(2-mesyloxyethoxy)-11β,17,21-trihydroxypregn-4-ene-3,20-dione, 21-acetate.

Workup

  1. extractionextracted with chloroform
  2. extractionThe chloroform extract
  3. customis dried
  4. customevaporated
  5. customto give an oil which
  6. customis chromatographed on a 20 g
  7. washElution with chloroform

Sources & evidence

ORD record
ord-c3cc9fb13a5141fcba7463991065bbe6
Source dataset
uspto-grants-1976_07
Patent number
US03971772

Reaction notes

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