Hydrochloric Acid → Methyl O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosinate
Reaction equation
[NH2:1][C@H:2]([C:22]([OH:24])=[O:23])[CH2:3][C:4]1[CH:11]=[C:9]([I:10])[C:8]([O:12][C:13]2[CH:20]=[C:18]([I:19])[C:17]([OH:21])=[C:15]([I:16])[CH:14]=2)=[C:6]([I:7])[CH:5]=1.Cl.[CH3:26]O>>[CH3:26][O:23][C:22](=[O:24])[C@H:2]([CH2:3][C:4]1[CH:5]=[C:6]([I:7])[C:8]([O:12][C:13]2[CH:14]=[C:15]([I:16])[C:17]([OH:21])=[C:18]([I:19])[CH:20]=2)=[C:9]([I:10])[CH:11]=1)[NH2:1]Participants
4
Procedure
Thyroxine (20 g) was suspended in dry methanol (500 ml). The suspension was saturated with hydrogen chloride gas, cooled and saturated again. The crystals were collected, washed with methanol and ether, and then dried. The resulting thyroxine methyl ester hydrochloride crystals were added to 500 ml of methanol and an equimolar concentration of concentrated sodium hydroxide was added with stirring. Deionized distilled water (500 ml) was added to this solution. The solution was chilled to recrystallize the thyroxine methyl ester from the solution. The crystals were then collected and air dried.
Workup
- temperaturecooled
- customThe crystals were collected
- washwashed with methanol and ether
- customdried
- additionThe resulting thyroxine methyl ester hydrochloride crystals were added to 500 ml of methanol
- concentrationan equimolar concentration of concentrated sodium hydroxide
- additionwas added
- distillationDeionized distilled water (500 ml)
- additionwas added to this solution
- temperatureThe solution was chilled
- customto recrystallize the thyroxine methyl ester from the solution
- customThe crystals were then collected
- customair dried
Sources & evidence
- ORD record
- ord-3dc5521c5a084d5c8e1af3efd73a5b34
- Source dataset
- uspto-grants-1988_01
- Patent number
- US04719182
Reaction notes
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