Proclavaminic acid → 3-Hydroxy-5-guanidino-2-(2-oxoazetidin-1-yl)pentanoic acid
Reaction equation
[CH2:1]1[C:4](=[O:5])[N:3]([C@H:6]([C:12]([OH:14])=[O:13])[C@H:7]([OH:11])[CH2:8][CH2:9][NH2:10])[CH2:2]1.NN=CS(O)(=O)=O.[NH:22](CCC[C@H](N1CCC1=O)C(O)=O)[C:23](N)=[NH:24]>>[OH:11][CH:7]([CH2:8][CH2:9][NH:10][C:23]([NH2:24])=[NH:22])[CH:6]([N:3]1[CH2:2][CH2:1][C:4]1=[O:5])[C:12]([OH:14])=[O:13]Participants
4
Procedure
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).
Sources & evidence
- ORD record
- ord-e75e581967c14549901e65ff874c8d5b
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05869299
Reaction notes
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