Cyclopentanecarboxylic acid, 2-oxo-, methyl ester → HCID 68540960, compound

HRID 1441952Notes

Reaction equation

HRID 1441952 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH3:10])=[O:8].[N:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1(C)C=CC=CC=1>[CH2:16]([O:15][C:13]([N:12]([C:3]1([C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])[NH:11][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 68540960HCID 68540960, compoundYield 130.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 2-oxocyclopentanecarboxylate (15.6 mg, 0.11 mmol) and (R,R)-trans-1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(N,N-dimethylamino)cyclohexyl]thiourea (4.1 mg, 0.01 mmol) in toluene (1 mL) was added diethyl azodicarboxylate (45.5 μL, 0.10 mmol) at room temperature. After stirring for 0.5 hr, the reaction mixture was concentrated. The residue was purified by silica gel column (hexane/ethyl acetate=3/1) to give the title compound (41.4 mg, yield: 92%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by silica gel column (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-de308b62f985419eb37c292574695f93
Source dataset
uspto-grants-2010_02
Patent number
US07655817B2

Reaction notes

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