Perchloric Acid → Acetoacetic Acid

HRID 1589957Notes

Reaction equation

HRID 1589957 reaction equation
[CH3:1][C@@:2]12[C@@:10]([OH:15])([C:11]([CH2:13][OH:14])=[O:12])[C@H:9]([OH:16])[CH2:8][C@H:7]1[C@@H:6]1[CH2:17][CH2:18][C:19]3[C@@:25]([CH3:26])([C@@:5]1([F:27])[C@@H:4]([OH:28])[CH2:3]2)[CH:24]=[CH:23][C:21](=[O:22])[CH:20]=3.Cl(O)(=O)(=O)=[O:30]>ClCCl>[CH3:1][C@@:2]12[C@@:10]([OH:15])([C:11]([CH2:13][OH:14])=[O:12])[C@H:9]([OH:16])[CH2:8][C@H:7]1[C@@H:6]1[CH2:17][CH2:18][C:19]3[C@@:25]([CH3:26])([C@@:5]1([F:27])[C@@H:4]([OH:28])[CH2:3]2)[CH:24]=[CH:23][C:21](=[O:22])[CH:20]=3.[C:10]([CH2:11][C:13]([OH:30])=[O:14])(=[O:15])[CH3:2]

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 31307Triamcinolone

Product 2

HCID 96Acetoacetic AcidHCID 31307Triamcinolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(VI) or triamcinolone is reacted with an acetylalkanoic acid in a solution of dichloromethane in the presence of catalytic amount of perchloric acid to produce the corresponding 16α,17-carboxycyclic acetal pregnane derivatives, e.g., when triamcinolone and acetylacetic acid are used the product is (XVI) 9α-fluoro-11β,21-dihydroxy-3,20-dioxo-16α, 17-(methyl, carboxylicmethyl)methylenedioxy-1,4-pregnadiene; when triamcinolone and acetylbutyric acid are used the product is (XVII) 9α-fluoro-11β,21-dihydroxy-3,20-dioxo-16α,17-(methyl, carboxylic-n-propyl)methylenedioxy-1,4-pregnadiene; (XVII) is reacted with diazomethane to produce same (VIII);

Sources & evidence

ORD record
ord-bbb3848d005045699cb7f285ad9cc584
Source dataset
uspto-grants-1993_04
Patent number
US05200518

Reaction notes

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