Hydrochloric Acid → 21-Chloro-11beta,17-dihydroxy-16alpha-(2-mesyloxyethoxy)pregna-1,4-diene-3,20-dione

HRID 918417Notes

Reaction equation

HRID 918417 reaction equation
[Cl:1][CH2:2][C:3](=[O:30])[C@:4]1([OH:29])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C@@H:19]([OH:23])[CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:24])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][C@H:5]1[O:25][CH2:26][CH2:27][OH:28].[CH3:31][S:32](Cl)(=[O:34])=[O:33].Cl>N1C=CC=CC=1>[Cl:1][CH2:2][C:3](=[O:30])[C@:4]1([OH:29])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C@@H:19]([OH:23])[CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:24])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][C@H:5]1[O:25][CH2:26][CH2:27][O:28][S:32]([CH3:31])(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 8673376021-Chloro-11beta,17-dihydroxy-16alpha-(2-hydroxyethoxy)pregna-1,4-diene-3,20-dione

Product 1

HCID 8673376121-Chloro-11beta,17-dihydroxy-16alpha-(2-mesyloxyethoxy)pregna-1,4-diene-3,20-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 21-chloro-11β,17-dihydroxy-16α-(2-hydroxyethoxy)pregna-1,4-diene-3,20-dione (7.6 mmoles) in 30 ml of pyridine is cooled to 0°C and 1 ml of methanesulfonyl chloride is added. After 2 hours the mixture is poured into cold dilute hydrochloric acid and extracted with chloroform. The chloroform solution is dried and evaporated in vacuo to yield the title compound.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe chloroform solution is dried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-ce70573a3aed435a8288f2b2e7890bd9
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

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