Water → HCID 68106173, compound

HRID 2403612Notes

Reaction equation

HRID 2403612 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][OH:3].[H-].[Na+].[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]([N:21]([CH2:23][C:24]1[CH:25]=[C:26]([C:30]2[CH:31]=[N:32][C:33]([N:36]3[CH2:41][CH2:40][N:39]([C:42](OC4C=CC([N+]([O-])=O)=CC=4)=[O:43])[CH2:38][CH2:37]3)=[N:34][CH:35]=2)[CH:27]=[CH:28][CH:29]=1)[CH3:22])=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].O>CN(C=O)C>[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]([N:21]([CH2:23][C:24]1[CH:25]=[C:26]([C:30]2[CH:31]=[N:32][C:33]([N:36]3[CH2:41][CH2:40][N:39]([C:42]([O:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])=[O:43])[CH2:38][CH2:37]3)=[N:34][CH:35]=2)[CH:27]=[CH:28][CH:29]=1)[CH3:22])=[O:20])=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 68106230HCID 68106230, compound

Product 1

HCID 68106173HCID 68106173, compoundYield 10.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Ethyl glycolate (116 mg) was dissolved in DMF (4 ml), and NaH (73 mg) was added thereto under ice-cooling. After stirring at the same temperature for 10 minutes, a solution of 4-nitrophenyl 4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazine-1-carboxylate (340 mg) in DMF (3 ml) was added thereto, followed by stirring at room temperature overnight. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over MgSO4, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2-ethoxy-2-oxoethyl 4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazine-1-carboxylate (35 mg).

Workup

  1. temperatureunder ice-cooling
  2. stirringby stirring at room temperature overnight
  3. extractionfollowed by extraction with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ba7805edaed7465596499de547419d29
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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