Liothyronine → N-Bromoacetyl-3,3',5-triiodothyronine

HRID 1681295

Reaction equation

HRID 1681295 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([I:23])[C:13]=1[O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([I:22])[CH:16]=1)[CH2:5][C@@H:6]([C:8]([OH:10])=[O:9])[NH2:7].[Br:24][CH2:25][C:26](Br)=[O:27]>C(OCC)(=O)C>[Br:24][CH2:25][C:26]([NH:7][C@H:6]([C:8]([OH:10])=[O:9])[CH2:5][C:4]1[CH:3]=[C:2]([I:1])[C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([I:22])[CH:16]=2)=[C:12]([I:23])[CH:11]=1)=[O:27]

Participants

4

Reactant 2

HCID 5920LiothyronineHCID 61147Bromoacetyl bromide

Product 1

HCID 122086N-Bromoacetyl-3,3',5-triiodothyronine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

According to the present invention a solution of 3,3',5-triiodo-L-thyronine and bromoacetyl bromide in ethyl acetate is refluxed for a period of time to produce the bromoacetylated hormone which is then fractionated by high speed countercurrent chromatography to yield highly pure N-bromoacetyl-3,3',5-triiodo-L-thyronine.

Workup

  1. temperatureis refluxed for a period of time
  2. customto produce the bromoacetylated hormone which

Sources & evidence

ORD record
ord-5970f06b834348c39766db5e4bc8499b
Source dataset
uspto-grants-1992_12
Patent number
US05169984

Linked notes

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