Isobutyl 4-oxobutanoate → (3R,S)-2,5-Dioxo-3-methylhexahydro-1H-pyrrolo[1,2-a]imidazole

HRID 1589806Notes

Reaction equation

HRID 1589806 reaction equation
Cl.[NH2:2][CH:3]([C:5]([NH2:7])=[O:6])[CH3:4].[O:8]=[CH:9][CH2:10][CH2:11][C:12](OCC(C)C)=O>>[O:6]=[C:5]1[C@@H:3]([CH3:4])[N:2]2[C:9](=[O:8])[CH2:10][CH2:11][C@H:12]2[NH:7]1

Participants

3

Reactant 2

HCID 10464575Isobutyl 4-oxobutanoateHCID 123172862-Aminopropanamide hydrochloride

Product 1

HCID 67887209(3R,S)-2,5-Dioxo-3-methylhexahydro-1H-pyrrolo[1,2-a]imidazole

Procedure

DL-Alaninamide hydrochloride (6.9 g, 0.055 mol) and isobutyl 4-oxobutanoate (7.3 g, 0.046 mol) were reacted together according the procedure of Example 2 to give the title compound, 1.7 g (24%), m.p. 84°-86°. NMR (DMSO-d6): deltaH =8.55 (bs, 1H, NH); 5.20 (t, J=5 Hz, NCHNH); 3.92 (q, J=6.5 Hz, 1H, CHCH3); 2.82-1.50 (c.a., 4H, CH2CH2); 1.17 (d, J=6.5 Hz, 3H, CHCH3). MS (E.I., 70 eV, 1.5 mA) m/z=154 (M+), 111 (M-CHNO)+, 98 (M-C3H4O)+.

Sources & evidence

ORD record
ord-08a296eb139b4583ad52101ca6bcf72d
Source dataset
uspto-grants-1993_04
Patent number
US05200406

Reaction notes

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