Diethyl Malonate → HCID 22718000, compound

HRID 1368877Notes

Reaction equation

HRID 1368877 reaction equation
[O-]CC.[Na+].[C:5]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30]Br)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]([O:13][CH2:14][CH3:15])=[O:12])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 22714477Benzyl (4-bromobutyl)carbamate

Product 1

HCID 22718000HCID 22718000, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

An ethanol (130.2 ml) solution of sodium ethoxide (5.83 g) was added with diethyl malonate (13 ml) and stirred at room temperature for 5 minutes. This solution was added with an ethanol (55.8 ml) solution of the 1-benzyloxycarbonylamino-4-bromobutane (4.9 g) obtained in the above step (b), and stirred at 40° C. for 20 hours. The reaction system was concentrated under reduced pressure without any treatment, and the residue was added with saturated aqueous ammonium chloride, and then the organic substances were extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (1.2 kg, hexane:ethyl acetate=2:1) to obtain diethyl 2-(4-benzyloxycarbonylaminobutyl)malonate (5.2 g, 83%).

Workup

  1. customobtained in the above step (b)
  2. stirringstirred at 40° C. for 20 hours
  3. concentrationThe reaction system was concentrated under reduced pressure without any treatment
  4. additionthe residue was added with saturated aqueous ammonium chloride
  5. extractionthe organic substances were extracted with ethyl acetate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (1.2 kg, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-871dc7748d584c8dbea3774c50f366b2
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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