Hydrochloric Acid → Pregna-1,4,9(11)-triene-3,20-dione, 21-chloro-16-methyl-, (16α)-

HRID 650507Notes

Reaction equation

HRID 650507 reaction equation
CS(Cl)(=O)=O.C[CH:7](O)[C:8](=[O:30])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C:23](=[CH:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH:19]=[CH:20]2)[CH2:15][CH2:14]3)[CH2:11][C@H:10]1[CH3:29].[ClH:32]>CC1C(CC)=NC=CC=1>[Cl:32][CH2:7][C:8](=[O:30])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C:23](=[CH:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH:19]=[CH:20]2)[CH2:15][CH2:14]3)[CH2:11][C@H:10]1[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 131722831HCID 131722831, compound

Product 1

HCID 15380094Pregna-1,4,9(11)-triene-3,20-dione, 21-chloro-16-methyl-, (16α)-

Reagents, catalysts & solvents 1

HCID 64277152-ethyl-3-methylpyridineSolvent

Procedure

8.8 ml of methane sulphonyl chloride is added at 10° C. to a mixture, under an inert atmosphere, of 15 g of methyl 16α-methyl-21-hydroxy-pregna-1,4,9(11)-triene-3-20-dione in 40 ml of methyl ethyl pyridine, and the whole is agitated at ambient temperature for 5 hours. It is poured into an ice+water mixture, acidified by the addition of hydrochloric acid, filtration is carried out, followed by washing and drying. 16.2 g of expected crude product is obtained which is purified by chromatography, eluting with a benzene/ethyl acetate mixture 8/2. 13.4 g of expected pure product is obtained. M.P.=154° C.

Workup

  1. washby washing
  2. customdrying

Sources & evidence

ORD record
ord-0654ffa02d9d44e297a5d574c59d6a2f
Source dataset
uspto-grants-2001_08
Patent number
US06274572B1

Reaction notes

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