Triethylamine → HCID 22798815, compound

HRID 441928Notes

Reaction equation

HRID 441928 reaction equation
Cl.[NH2:2][C@H:3]([C:23]([OH:25])=[O:24])[CH2:4][C:5]1[CH:12]=[C:10]([I:11])[C:9]([O:13][C:14]2[CH:21]=[C:19]([I:20])[C:18]([OH:22])=[C:16]([I:17])[CH:15]=2)=[C:7]([I:8])[CH:6]=1.[CH2:26](N(CC)CC)C.[C:33]1(=[O:40])[O:39][C:37](=[O:38])[CH2:36][O:35][CH2:34]1>C1COCC1.C(Cl)(Cl)Cl>[CH3:26][O:24][C:23](=[O:25])[C@H:3]([CH2:4][C:5]1[CH:6]=[C:7]([I:8])[C:9]([O:13][C:14]2[CH:15]=[C:16]([I:17])[C:18]([OH:22])=[C:19]([I:20])[CH:21]=2)=[C:10]([I:11])[CH:12]=1)[NH:2][C:33](=[O:40])[CH2:34][O:35][CH2:36][C:37]([OH:39])=[O:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 782321,4-Dioxane-2,6-dioneHCID 67240529HCID 67240529, compound

Product 1

HCID 22798815HCID 22798815, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.65g of the methyl ester of thyroxine hydrochloride in 80ml of dry THF and 30ml of chloroform in a flask protected from light was injected 300μl of triethylamine while the mixture was agitated. Diglycolic anhydride (255mg, 0.0022 mole) was then added and the mixture stirred overnight. The solution was then washed 3 times with water, dried over sodium sulphate and the volatiles removed in vacuo. The residue was purified on a 30g Sephadex LH-20 column, using a solution of 20% methanol in dichloromethane as eluent. The clear fractions were collected, the solvent removed and the residue precipitated from methanol with water, yielding 1.53g, 84 percent.

Workup

  1. stirringthe mixture stirred overnight
  2. washThe solution was then washed 3 times with water
  3. dry with materialdried over sodium sulphate
  4. customthe volatiles removed in vacuo
  5. customThe residue was purified on a 30g Sephadex LH-20 column
  6. customThe clear fractions were collected
  7. customthe solvent removed
  8. customthe residue precipitated from methanol with water
  9. customyielding 1.53g, 84 percent

Sources & evidence

ORD record
ord-34f2acd6009c4dff98e16fa7a1d43c47
Source dataset
uspto-grants-1977_08
Patent number
US04043872

Reaction notes

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