Thyroxine → Methyl thyroxinate hydrochloride

HRID 1886005Notes

Reaction equation

HRID 1886005 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.[CH3:25]O.[ClH:27]>>[ClH:27].[NH2:1][C@H:2]([C:22]([O:24][CH3:25])=[O:23])[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

Participants

3

Reactant 2

HCID 5819ThyroxineHCID 21893726Hydrochloride methanol

Product 1

HCID 13911220Methyl thyroxinate hydrochloride

Procedure

Thyroxine (1 g) was dissolved in the methanol/HCl, to which molecular sieve was added, and the mixture was left at room temperature overnight. The ester precipitates out with a yield of above 90%. After filtration, the product was washed with acetone and stored in a vacuum desiccator until use.

Workup

  1. additionwas added
  2. customThe ester precipitates out with a yield of above 90%
  3. filtrationAfter filtration
  4. washthe product was washed with acetone

Sources & evidence

ORD record
ord-d6281931c4fc4c948c88050d3cce5aa0
Source dataset
uspto-grants-1992_09
Patent number
US05149630

Reaction notes

Loading…