Hydrochloric Acid → HCID 70447346, compound
Reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([O:8][C:9]2[C:14]([I:15])=[CH:13][C:12]([CH2:16][CH:17]([NH2:21])[C:18]([OH:20])=[O:19])=[CH:11][C:10]=2[I:22])[CH:2]=1.[ClH:23].[CH3:24]O>>[ClH:23].[CH3:24][O:19][C:18](=[O:20])[C@H:17]([CH2:16][C:12]1[CH:11]=[C:10]([I:22])[C:9]([O:8][C:3]2[CH:4]=[CH:5][C:6]([OH:7])=[CH:1][CH:2]=2)=[C:14]([I:15])[CH:13]=1)[NH2:21]Participants
Procedure
Five g (9.52 mmoles) of L-3,5-diiodothyronine (Sigma Chemical Company, St. Louis, Mo. 63178, Catalog No. D0629) was suspended in 50 ml of methanol (MCB, Norwood, Ohio 45212, Catalog No. MX0488-1). Dry hydrogen chloride was bubbled through the resulting suspension until the methanol was saturated with hydrogen chloride. The mixture warmed as the 3,5-diiodothyronine dissolved, resulting in a yellowish-green solution. The reaction mixture was allowed to stand for 16 hours at ambient temperature in a closed vessel. Dry hydrogen chloride was again passed through the reaction mixture. The reaction mixture was allowed to stand for an additional six hours in a closed vessel. The methanol was allowed to evaporate from the reaction mixture in a fume hood at ambient temperature, leaving 5.2 g (95% yield) of white, crystalline powder, 3,5-diiodothyronine methyl ester hydrochloride.
Workup
- customDry hydrogen chloride was bubbled through the resulting suspension until the methanol
- temperatureThe mixture warmed as the 3,5-diiodothyronine
- dissolutiondissolved
- customresulting in a yellowish-green solution
- waitto stand for an additional six hours in a closed vessel
- customto evaporate from the reaction mixture in a fume hood at ambient temperature
Sources & evidence
- ORD record
- ord-d89fb6d9dea14dda8ebe4b0703ae7460
- Source dataset
- uspto-grants-1987_12
- Patent number
- US04711855
Reaction notes
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