Proclavaminic acid → 3-Hydroxy-5-guanidino-2-(2-oxoazetidin-1-yl)pentanoic acid

Participants

Reaction Steps

Proclavaminic acid (84.5 mg, 0.42 mmol) was treated aminoiminomethane-sulphonic acid in the fashion described above for the preparation 5-guanidino-2-(2-oxoazetidin-1-yl)pentanoic acid (Compound B) to give 3-hydroxy-5-guanidino-2-(2-oxoazetidin-1-yl)pentanoic acid as a white solid (62 mg, 53%), (Found: C, 38.76; H, 6.83; N, 19.54. C9H16N4O4. 2H2O requires: C, 38.57; H, 7.19; N, 19.99% (FAB; thioglycerol) MH+ 245, C9H16N4O4 requires 245; νmax.(KBr) 3 363, 1 719, 1 673, and 1 600cm-1, δH(400 MHz; D2O) 1.73-1.93 (2H, m, 4-H), 3.07(2H, t, J=4.0 Hz, 3'-H), 3.41 (2H, t, J=6.5 Hz, 5-H), 3.42-3.60 (1H, m), 3.60-3.68 (1H, m) 4'-H), 4.12 (1H, d, J=5.4 Hz, 2-H), 4.22 (1H, m, 3-H).

Provenance & Evidence