Ammonia → 2-Carbamoylmethyl-2-(pyrrol-1-yl)malonic acid diethyl ester

HRID 256584Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH2:16][C:17](O)=[O:18])([N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].O[N:22]1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.N>ClCCl.C(#N)C>[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH2:16][C:17](=[O:18])[NH2:22])([N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-carboxymethyl-2-(pyrrol-1-yl)-malonic acid diethyl ester (36.0 g), N-hydroxysuccinimide (16.1 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (29.2 g) in dichloromethane (200 ml) was stirred at 25° C. for 1 hour, followed by addition of 7.8% (w/w) ammonia in acetonitrile (110 ml). The resulting mixture was stirred at 25° C. for 1 hour and concentrated under reduced pressure at the same temperature. The residue was dissolved in ethyl acetate. The solution was washed with 5% hydrochloric acid and then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give the title compound (29.0 g, 80.8%) as colorless crystals, mp 94°-95° C.

Workup

stirringThe resulting mixture was stirred at 25° C. for 1 hour
concentrationconcentrated under reduced pressure at the same temperature
dissolutionThe residue was dissolved in ethyl acetate
washThe solution was washed with 5% hydrochloric acid
dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-dcb2e26efaf8480e98022fe73a602213
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258382

Reaction notes

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