Sodium hydride → HCID 90281999, compound

HRID 1497505Notes

Reaction equation

HRID 1497505 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]1[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])=[CH:25][CH:26]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 90282072HCID 90282072, compound

Product 1

HCID 90281999HCID 90281999, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-(2-{[(benzyloxy)carbonyl]amino}ethyl)benzoate (515 mg) in N,N-dimethylformamide (10.0 mL) was added 55% sodium hydride (65.0 mg) under ice-cooling, followed by stirring for 30 minutes under ice-cooling. Under ice-cooling, tert-butyl bromoacetate (0.300 mL) was added thereto, followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous ammonium chloride solution under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 4-(2-{[(benzyloxy)carbonyl](2-tert-butoxy-2-oxoethyl)amino}ethyl)benzoate (473 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperatureUnder ice-cooling
  4. stirringby stirring at room temperature overnight
  5. temperaturecooling
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationThe solvent was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-50333dd3162d497d9b0ae8c6f0b7f0ed
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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