Sodium hydride → HCID 18385404, compound

HRID 1250212Notes

Reaction equation

HRID 1250212 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:22])[CH:14]=2)[N:10]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][CH:24]=2)[C:9]1=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:34][CH2:35][CH2:36][CH2:37][N:38]1[C:42](=[O:43])[C:41]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:40]2[C:39]1=[O:48].[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH3:22])[CH:14]=2)[N:10]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH2:34][CH2:35][CH2:36][CH2:37][N:38]3[C:42](=[O:43])[C:41]4[C:40](=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:39]3=[O:48])[CH:24]=2)[C:9]1=[O:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 93575N-(4-Bromobutyl)phthalimideHCID 18385439HCID 18385439, compound

Product 1

HCID 18385404HCID 18385404, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of step e) (0.034 g, 0.080 mmol), N-(4-bromobutyl)phthalimide (0.028 g, 0.10 mmol) and sodium hydride (95%, 0.0024 g, 0.10 mmol) was dissolved in dry DMF (0.5 ml). After stirring at room temperature for 1.5 hour HPLC shows complete reaction. The reaction was quenched by addition of aqueous acetic acid (1 M, 2 ml) and ethyl acetate (2 ml), the phases were separated and the organic phase washed with water (1×2 ml). Solvent removal followed by chromatographic purification on silica, eluting with heptane—ethyl acetate (20:80), furnishes the sub-title product (0.019 g, 38%) as a slightly brown solid.

Workup

  1. customreaction
  2. customThe reaction was quenched by addition of aqueous acetic acid (1 M, 2 ml) and ethyl acetate (2 ml)
  3. customthe phases were separated
  4. washthe organic phase washed with water (1×2 ml)
  5. customSolvent removal
  6. customfollowed by chromatographic purification on silica
  7. washeluting with heptane—ethyl acetate (20:80)

Sources & evidence

ORD record
ord-2af3a4c464e54202b07d2e2236f5f248
Source dataset
uspto-grants-2002_01
Patent number
US06337342B1

Reaction notes

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