Triethylamine → 1-[[(2-Oxo-1-imidazolidinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester

HRID 448736

Reaction equation

[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[C:7](Cl)=[O:8].[C:10]1([CH2:16][O:17][C:18]([C:20]2([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:10]1([CH2:16][O:17][C:18]([C:20]2([NH:26][C:7]([N:3]3[CH2:4][CH2:5][NH:6][C:2]3=[O:1])=[O:8])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)=[O:19])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1.38 g (9.3 mmol) of 2-oxo-1-imidazolidinecarbonyl chloride was added to a solution of 2.17 g (9.3 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester and 1.04 g (10 mmol) of triethylamine in 100 ml of chloroform, and the mixture was stirred at 60° C. for 4 days. The reaction solution was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained crystal was washed with diethyl ether to obtain 2.64 g (82%) of the title compound.

Workup

washThe reaction solution was successively washed with water
dry with materiala 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and it was dried with anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
washthe obtained crystal was washed with diethyl ether

Sources & evidence

ORD record: ord-8c73fb65a01a4bbc84455997d35dca8d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481725B2

Linked notes

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