Iodine → Thyroxine

HRID 410125

Reaction equation

[Na:1][Na].[NH2:3][C@H:4]([C:24]([OH:26])=[O:25])[CH2:5][C:6]1[CH:13]=[C:11]([I:12])[C:10]([O:14][C:15]2[CH:22]=[C:20]([I:21])[C:19]([OH:23])=[C:17]([I:18])[CH:16]=2)=[C:8]([I:9])[CH:7]=1.II.[OH-].[Na+]>>[Na+:1].[Na+:1].[NH2:3][C@H:4]([C:24]([O-:26])=[O:25])[CH2:5][C:6]1[CH:7]=[C:8]([I:9])[C:10]([O:14][C:15]2[CH:16]=[C:17]([I:18])[C:19]([OH:23])=[C:20]([I:21])[CH:22]=2)=[C:11]([I:12])[CH:13]=1.[NH2:3][C@H:4]([C:24]([O-:26])=[O:25])[CH2:5][C:6]1[CH:7]=[C:8]([I:9])[C:10]([O:14][C:15]2[CH:16]=[C:17]([I:18])[C:19]([OH:23])=[C:20]([I:21])[CH:22]=2)=[C:11]([I:12])[CH:13]=1.[NH2:3][C@H:4]([C:24]([OH:26])=[O:25])[CH2:5][C:6]1[CH:7]=[C:8]([I:9])[C:10]([O:14][C:15]2[CH:16]=[C:17]([I:18])[C:19]([OH:23])=[C:20]([I:21])[CH:22]=2)=[C:11]([I:12])[CH:13]=1

Participants

Reactant 4

HCID 807Iodine

HCID 5819Thyroxine2×

HCID 14798Sodium Hydroxide

HCID 141233Disodium

Product 2

HCID 5819Thyroxine

HCID 131731637L-thyroxine di-sodium salt

Procedure

FIG. 2: Preparation of the disodium salt of L-thyroxine (compound of Formula II) i.e. according to IT1302201 by iodination of compound of Formula I with KI/I2 in the presence of a suitable amine. The mono and di-potassium salts mixture is subjected to a subsequent separation and purification steps, including:(a) the addition of an organic acid; (b) the separation of the thus obtained “free form” (as a precipitate); and (c) the addition of an excess of sodium hydroxide to obtain the L-thyroxine di-sodium salt of Formula II.

Workup

customThe mono and di-potassium salts mixture is subjected to a subsequent separation and purification steps
addition(a) the addition of an organic acid
custom(b) the separation of the
customthus obtained “free form” (as a precipitate)

Sources & evidence

ORD record: ord-30b13a9f481147ce9b0b2bf9607f154b
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759572B2

Linked notes

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