Water → HCID 22861977, compound

HRID 260256Notes

Reaction equation

HRID 260256 reaction equation
[CH3:1][O:2][C:3](=[O:38])[C@H:4]([CH2:19][C:20]1[CH:27]=[C:25]([I:26])[C:24]([O:28][C:29]2[CH:36]=[C:34]([I:35])[C:33]([OH:37])=[C:31]([I:32])[CH:30]=2)=[C:22]([I:23])[CH:21]=1)[NH:5][C:6](=[O:18])[CH2:7][O:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].[C:39]1(=[O:46])[O:45][C:43](=[O:44])[CH2:42][O:41][CH2:40]1.O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:38])[C@H:4]([CH2:19][C:20]1[CH:21]=[C:22]([I:23])[C:24]([O:28][C:29]2[CH:30]=[C:31]([I:32])[C:33]([OH:37])=[C:34]([I:35])[CH:36]=2)=[C:25]([I:26])[CH:27]=1)[NH:5][C:6](=[O:18])[CH2:7][O:8][CH2:9][C:10]([N:12]1[CH2:13][CH2:14][N:15]([C:43](=[O:44])[CH2:42][O:41][CH2:40][C:39]([OH:46])=[O:45])[CH2:16][CH2:17]1)=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 782321,4-Dioxane-2,6-dioneHCID 22861981HCID 22861981, compound

Product 1

HCID 22861977HCID 22861977, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

N-(Piperazinocarbonylmethoxyacetyl)thyroxine methyl ester from step 1 (3.1 g, 0.0034 mole) and diglycolic anhydride (0.6 g, 0.0046 mole) in chloroform (200 mL) were heated to 50°-60° C. (hot water) and allowed to stir at ambient temperature for 16 hours. Chloroform (200 mL) was added. The mixture was washed with 5% HCl solution (2×100 mL), water (100 mL), saturated NaCl solution (100 mL), dried over anhydrous magnesium sulfate, filtered, and the solvent removed on a rotary evaporator in vacuo. This material was used directly in the next step.

Workup

  1. washThe mixture was washed with 5% HCl solution (2×100 mL), water (100 mL), saturated NaCl solution (100 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed on a rotary evaporator in vacuo

Sources & evidence

ORD record
ord-2c30aae33b7f43c98b4bccc816910104
Source dataset
uspto-grants-1996_06
Patent number
US05527709

Reaction notes

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