Sodium Carbonate → HCID 10295069, compound

HRID 1168101Notes

Reaction equation

HRID 1168101 reaction equation
Br[CH2:2][C:3]1[CH:19]=[C:18]([Cl:20])[C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH:15]([CH3:17])[CH3:16])[CH:9]=2)=[C:5]([Cl:21])[CH:4]=1.[O:22]1[C:26](=[O:27])[NH:25][C:24](=[O:28])[NH:23]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.Cl>[Cl:21][C:5]1[CH:4]=[C:3]([CH:19]=[C:18]([Cl:20])[C:6]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH:15]([CH3:17])[CH3:16])[CH:9]=1)[CH2:2][N:23]1[C:24](=[O:28])[NH:25][C:26](=[O:27])[O:22]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3330851,2,4-oxadiazolidine-3,5-dioneHCID 22285674HCID 22285674, compound

Product 1

HCID 10295069HCID 10295069, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the title compound of Step B (59 mg, 0.15 mmol) and [1,2,4]oxadiazolidine-3,5-dione (16 mg, 0.15 mmol) in DMF (1.5 ml) at room temperature was added sodium carbonate (32 mg, 0.30 mmol). After stirring at room temperature for about two hours, the solution was diluted with 0.5N HCl (10 ml) and extracted with ethyl acetate (3×10 ml). The combined organic extracts were washed with water (3×15 ml), brine (15 ml), dried, filtered, and concentrated. The crude product was purified by preparative TLC (22% methanol/3.5% water/74.5% chloroform) to afford the title compound (61 mg). MS (APCl−) Calc: 410.0, found: 409.1 (M−1).

Workup

  1. extractionextracted with ethyl acetate (3×10 ml)
  2. washThe combined organic extracts were washed with water (3×15 ml), brine (15 ml)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative TLC (22% methanol/3.5% water/74.5% chloroform)

Sources & evidence

ORD record
ord-1b443912dd764a22b7b566f135d16737
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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