Diethyl Ether → 4-(benzylcarbamoyl)butanoic Acid

HRID 467269Notes

Reaction equation

HRID 467269 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)C>ClCCl>[O:6]=[C:5]([NH:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7504BenzylamineHCID 7940Glutaric anhydride

Product 1

HCID 36055364-(benzylcarbamoyl)butanoic AcidYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 25 gm (220 mMol) glutaric anhydride in dichloromethane (250 ml) was added a solution of 26.4 ml (242 mMol) benzylamine in dichloromethane (50 ml) dropwise. The reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was then poured into diethyl ether (500 ml) and the resulting solid was filtered. The filter cake was washed with diethyl ether, dried under vacuum and then recrystallized from ethyl acetate to give 24.8 gm (51%) 5-oxo-5-(phenylmethylamino)pentanoic acid as a crystalline solid.

Workup

  1. filtrationthe resulting solid was filtered
  2. washThe filter cake was washed with diethyl ether
  3. customdried under vacuum
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-de05faa74b6746a99e21aa8038ce52b4
Source dataset
uspto-grants-1992_10
Patent number
US05159081

Reaction notes

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