2-Methylpropyl 3-carbamoylmethyl-Beta-hydroxy2-(1-methylethyl)-4-oxo-1-imidazolidinebutanoate → N-(2-Amino-2-oxoethyl)-2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetamide

HRID 1608017Notes

Reaction equation

[C:1]([CH2:4][N:5]1[C:9](=[O:10])[CH2:8][N:7]([CH2:11][CH:12]([OH:21])[CH2:13][C:14](OCC(C)C)=[O:15])C1C(C)C)(=[O:3])[NH2:2]>CN(C)C=O.O>[OH:21][CH:12]1[CH2:11][N:7]([CH2:8][C:9]([NH:5][CH2:4][C:1]([NH2:2])=[O:3])=[O:10])[C:14](=[O:15])[CH2:13]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 11.8 g (34.3mol) of 2-methylpropyl 3-carbamoylmethyl-Beta-hydroxy-2-(l-methylethyl)-4-oxo-1-imidazolidinebutanoate in 90 ml of dimethylformamide and 10 ml of water was gently refluxed (external temp. 130° C.) for 24 hours. The solvent was evaporated under reduced pressure. The oily residue was taken up with 40 ml of ethanol and stirred at 0° C. for 30 minutes. The precipitate was collected and crystallized from ethanol/isopropanol 1:1 to give 2.5 g of the title compound as a white powder, m.p. 158°-160° C. Mass spectrum (E.I., 70 eV, 1.5 mA), m/z=197 (M+ --H2O), 180. IR spectrum (oil mull): 3420, 3320, 3220, 1680, 1655 and 1630 cm`31.

Workup

customThe solvent was evaporated under reduced pressure
customThe precipitate was collected
customcrystallized from ethanol/isopropanol 1:1

Sources & evidence

ORD record: ord-da08c7ac608949e6b0cdbe740efd051b
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04868313

Reaction notes

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