Potassium Carbonate → HCID 13519821, compound

HRID 371332Notes

Reaction equation

HRID 371332 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCOCC>[O:7]=[C:1]1[CH2:2][CH2:3][C:4](=[O:6])[N:5]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11439SuccinimideHCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 13519821HCID 13519821, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of succinimide (1, 3.2 g, 31.6 mmol) and ethyl 7-bromoheptanoate (5 g, 21 mmol) in dimethylformamide (30 mL) containing potassium carbonate (3.5 g, 25 mmol) was heated at about 55° to 60° C. for twenty hours. The mixture was then diluted with ether and washed twice with water, once with saturated aqueous sodium chloride, and dried over magnesium sulfate. Removal of the solvent under reduced pressure gave the crude product which was purified by high performance liquid chromatography (HPLC) to give 3.66 g of 7-(2-oxo-5-oxopyrrolidin-1-yl)heptanoic acid, ethyl ester, 2. IR (neat): 1775, 1735, 1700 cm-1 ; PMR (CDCl3): δ 4.10 (q, J=7, 2H), 3.46 (t, J=7, 2H), 2.67 (s, 4H), 2.26 (t, J=7, 2H), 1.77-1.11 (m, 8H), and 1.23 (t, J=7, 3H).

Workup

  1. temperaturewas heated at about 55° to 60° C. for twenty hours
  2. washwashed twice with water, once with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of the solvent under reduced pressure
  5. customgave the crude product which
  6. customwas purified by high performance liquid chromatography (HPLC)

Sources & evidence

ORD record
ord-9f0dd5619a544cb0ab5f6f8f0df2112e
Source dataset
uspto-grants-1985_07
Patent number
US04530933

Reaction notes

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