Succinic anhydride → HCID 22861971, compound

HRID 260255Notes

Reaction equation

HRID 260255 reaction equation
Br.[CH3:2][O:3][C:4](=[O:39])[C@H:5]([CH2:20][C:21]1[CH:28]=[C:26]([I:27])[C:25]([O:29][C:30]2[CH:37]=[C:35]([I:36])[C:34]([OH:38])=[C:32]([I:33])[CH:31]=2)=[C:23]([I:24])[CH:22]=1)[NH:6][C:7](=[O:19])[CH2:8][O:9][CH2:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:12].[C:40]1(=[O:46])[O:45][C:43](=[O:44])[CH2:42][CH2:41]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:2][O:3][C:4](=[O:39])[C@H:5]([CH2:20][C:21]1[CH:22]=[C:23]([I:24])[C:25]([O:29][C:30]2[CH:31]=[C:32]([I:33])[C:34]([OH:38])=[C:35]([I:36])[CH:37]=2)=[C:26]([I:27])[CH:28]=1)[NH:6][C:7](=[O:19])[CH2:8][O:9][CH2:10][C:11]([N:13]1[CH2:14][CH2:15][N:16]([C:40](=[O:46])[CH2:41][CH2:42][C:43]([OH:45])=[O:44])[CH2:17][CH2:18]1)=[O:12]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 86749570HCID 86749570, compound

Product 1

HCID 22861971HCID 22861971, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To N-(piperazinocarbonylmethoxyacetyl)thyroxine methyl ester Hydrobromide from step 5 (9.5 g, 0.01 mole) and succinic anhydride (2.0 g, 0.02 mole), in chloroform (400 mL) was added triethylamine (3.3 g, 0.033 mole). The slurry immediately begins to dissolve and the mixture was stirred overnight at room temperature. The next day the solid had all dissolved and the solution was washed with 5% HCl solution (3×100 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 further purified by chromatography using SiO2.

Workup

  1. dissolutionto dissolve
  2. dissolutionall dissolved
  3. washthe solution was washed with 5% HCl solution (3×100 mL), water (100 mL), saturated NaCl solution (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed on a rotary evaporator in vacuo
  7. customThis material was further purified by chromatography

Sources & evidence

ORD record
ord-ec99dfc419e94dada1fe4a9881f6a8cd
Source dataset
uspto-grants-1996_06
Patent number
US05527709

Reaction notes

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