Sodium hydride → HCID 69710152, compound

HRID 2121913Notes

Reaction equation

HRID 2121913 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][O:8][C:9]1[C:17]([CH2:18]Cl)=[C:16]2[C:12]([CH:13]=[N:14][N:15]2[CH2:20][C@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH3:22])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[C:1]([O:5][C:6]([CH:7]1[O:8][C:9]2=[CH:10][CH:11]=[C:12]3[C:16]([N:15]([CH2:20][C@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH3:22])[N:14]=[CH:13]3)=[C:17]2[CH2:18]1)=[O:31])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 69702056HCID 69702056, compound

Product 1

HCID 69710152HCID 69710152, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product from Step B (2.90 g, 6.18 mmol) in anhydrous 1-methyl-2-pyrrolidone (30 mL) was added sodium hydride (60%, 0.371 g, 9.27 mmol). The mixture was heated at 50° C. overnight and at ambient temperature for 2 days, cooled and poured into a saturated aqueous solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate. Chromatography on silica (gradient, 2% to 25% ethyl acetate in hexane) gave an oil (0.48 g, 18%): LC/MS (+APCI) m/z 433(M+H).

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-385b5b8d900c4a34aaff49055a0097b3
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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