Dicyclohexylcarbodiimide → Thyroxine

HRID 435514

Reaction equation

HRID 435514 reaction equation
C(O[NH:6][C@H:7]([C:27]([OH:29])=[O:28])[CH2:8][C:9]1[CH:16]=[C:14]([I:15])[C:13]([O:17][C:18]2[CH:25]=[C:23]([I:24])[C:22]([OH:26])=[C:20]([I:21])[CH:19]=2)=[C:11]([I:12])[CH:10]=1)(C)(C)C.ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[NH2:6][C@H:7]([C:27]([OH:29])=[O:28])[CH2:8][C:9]1[CH:10]=[C:11]([I:12])[C:13]([O:17][C:18]2[CH:19]=[C:20]([I:21])[C:22]([OH:26])=[C:23]([I:24])[CH:25]=2)=[C:14]([I:15])[CH:16]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 54358334HCID 54358334, compound

Product 1

HCID 5819Thyroxine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.23 g (1.4 mmoles) of N-(tert-butoxy)-L-thyroxine and 0.16 g (1.4 mmoles) of N-hydroxysuccinimide are dissolved in 20 mL dimethylformamide. 0.31 g (1.5 mmoles) of dicyclohexyl carbodiimide is added to the solution which is then stirred at room temperature for 18 h. The urea precipitated during the reaction is removed by filtration and the filtrate, containing the active ester, is stored at -20° C.

Workup

  1. customThe urea precipitated during the reaction
  2. customis removed by filtration
  3. additionthe filtrate, containing the active ester
  4. customis stored at -20° C.

Sources & evidence

ORD record
ord-766db094727d4f78be203c00f89a3ea5
Source dataset
uspto-grants-1983_08
Patent number
US04401765

Linked notes

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