Hydrochloric Acid → Thyroxine N-iodoacetamide

HRID 1455857Notes

Reaction equation

HRID 1455857 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.[OH-].[Na+].C1C(=O)[N:31](OC(CI)=O)[C:29](=[O:30])[CH2:28]1.Cl>CO.O.C(Cl)(Cl)Cl.CO.C(O)(=O)C>[NH2:1][C@H:2]([C:22]([OH:24])=[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.[I:7][NH:31][C:29](=[O:30])[CH3:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5819ThyroxineHCID 14798Sodium Hydroxide2×HCID 3299230Iodoacetic acid N-hydroxysuccinimide ester

Product 1

HCID 88342297Thyroxine N-iodoacetamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 21866353chloroform methanol HOAcSolvent

Procedure

78 mg (0.1 mmole) of L-thyroxine was dissolved in 1.0 ml of methanol on addition of 34 mls (0.2 mmole) of 6N NaOH and sonication in a bath sonicator. 48 mg of iodoacetic acid N-hydroxysuccinimide ester was added and the mixture vortexed. 8.5 mls of 6N NaOH was added and the mixture vortexed. TLC (chloroform:methanol:acetic acid 50:6:2 on silica gel) indicated complete reaction. 50 mls of 6N HCl was added and then 4 mls of water and formed a precipitate. The precipitate was collected by centrifugation and washed with 1 ml of methanol and 4 mls of water. After centrifugation the pellet was dried under vacuum to 82 mg of an off-white solid.

Workup

  1. customreaction
  2. customThe precipitate was collected by centrifugation
  3. washwashed with 1 ml of methanol and 4 mls of water
  4. dry with materialAfter centrifugation the pellet was dried under vacuum to 82 mg of an off-white solid

Sources & evidence

ORD record
ord-ac52f0db751c454eab937e669a073c1b
Source dataset
uspto-grants-1998_12
Patent number
US05843634

Reaction notes

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