1,4-Dioxane-2,6-dione → HCID 68151161, compound

HRID 1517172Notes

Reaction equation

HRID 1517172 reaction equation
[C:1]([O:5][C:6](=[O:45])[CH:7]([N:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:44])[NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][NH2:43])=[CH:26][CH:25]=1)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:46]1(=[O:53])[O:52][C:50](=[O:51])[CH2:49][O:48][CH2:47]1>CN(C)C=O>[C:1]([O:5][C:6](=[O:45])[CH:7]([N:11]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30](=[O:44])[NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][NH:43][C:50](=[O:51])[CH2:49][O:48][CH2:47][C:46]([OH:53])=[O:52])=[CH:28][CH:29]=1)[S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)(=[O:14])=[O:13])[CH:8]([CH3:9])[CH3:10])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 782321,4-Dioxane-2,6-dioneHCID 69450212HCID 69450212, compound

Product 1

HCID 68151161HCID 68151161, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the amine (Compound 13*; 60 mg, 0.092 mmol), N, N′-diisopropyl ethylamine (96 μl, 0.55 mmol), and diglycolic anhydride (66 mg, 0.55 mmol) in dimethylformamide (6 ml) was stirred at ambient temperature for 3 hours when monitoring by HPLC indicated complete reaction. The solvent was removed under reduced pressure and the residue dissolved in acetonitrile containing 0.1% TFA. After stirring for 5 minutes, the mixture was evaporated to dryness and the crude product purified by flash chromatography using CHCl3MeOH/H2O, 65:25:4. The product was obtained as white foam. Yield 70.50 mg (99.80%).

Workup

  1. customreaction
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue dissolved in acetonitrile containing 0.1% TFA
  4. stirringAfter stirring for 5 minutes
  5. customthe mixture was evaporated to dryness
  6. customthe crude product purified by flash chromatography
  7. customThe product was obtained as white foam

Sources & evidence

ORD record
ord-7d8b2b3b32ff4d778d929cca42aa0a51
Source dataset
uspto-grants-2012_07
Patent number
US08231858B2

Reaction notes

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