Sodium hydride → HCID 23121900, compound

HRID 1713507Notes

Reaction equation

HRID 1713507 reaction equation
CC([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]1([CH2:28]O)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:7])(C)C.[H-].[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O>[O:5]=[C:6]1[N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:10][C:9]2([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:28][O:7]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 69645660HCID 69645660, compound

Product 1

HCID 23121900HCID 23121900, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bis(1,1-dimethylethyl)2-(hydroxymethyl)-2-(phenylmethyl)piperazine-1,4-dicarboxylate (3.6 g, 8.9 mmol) was dissolved in N,N-dimethylformamide (40 mL). 60% Sodium hydride (0.43 g, 11 mmol) was added thereto, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added a 0.5 M aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue was added diethyl ether, and the precipitated crystals were collected by filtration to obtain the title compound (2.6 g, yield 88%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added diethyl ether
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-b45dc414ea564d77806b8014ba762f7b
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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