Sulfuric Acid → Colchicine, N-deacetyl-10-thio-

HRID 1418048Notes

Reaction equation

CC([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([S:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([O:28][CH3:29])=[C:11]([O:26][CH3:27])[C:12]=2[O:24][CH3:25])[CH2:7][CH2:6]1)=O.S(=O)(=O)(O)O>>[CH3:29][O:28][C:10]1[CH:9]=[C:8]2[CH2:7][CH2:6][C@H:5]([NH2:4])[C:21]3[C:14](=[CH:15][CH:16]=[C:17]([S:22][CH3:23])[C:18]([CH:20]=3)=[O:19])[C:13]2=[C:12]([O:24][CH3:25])[C:11]=1[O:26][CH3:27]

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 17648Thiocolchicine

Product 1

HCID 17649Colchicine, N-deacetyl-10-thio-

Procedure

In the case of thiocolchicine, the hydrolysis with hydrohalogen acids or, more preferably, with sulfuric acid (20% H2SO4 --120 h) allows one to obtain N-deacetylthiocolchicine and 3-demethyl-N-deacetylthiocolchicine in essentially quantitative yields.

Sources & evidence

ORD record: ord-94da5a9aacf24451a17d6921eb1e6ef7
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05880160

Reaction notes

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