Gamma-Aminobutyric Acid → 4-[3-Hydroxy-4(methoxy-naphthalen-1-yl methyl-carbamoyl)-2-oxo-2,5-dihydro-pyrrol-1-yl]-butyric acid
Reaction equation
COC(=O)C(O)=CC(=O)N(OC)C[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.C=O.NCCC[C:30](O)=[O:31].ClC1C=C(C=CC=1Cl)[CH2:37][N:38](OC)[C:39]([C:41]1[CH2:45][N:44]([CH2:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])[C:43](=[O:52])[C:42]=1[OH:53])=[O:40]>>[OH:53][C:42]1[C:43](=[O:52])[N:44]([CH2:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])[CH2:45][C:41]=1[C:39](=[O:40])[N:38]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH2:37][O:31][CH3:30]Participants
5
Reactant 4
Product 1
Procedure
2-Hydroxy-3-(methoxy-naphthalen-1-ylmethyl-carbamoyl)-acrylic acid methyl ester, paraformaldehyde and 4-amino-butyric acid were reacted using the method described for the synthesis of Compound 810 to give the title compound as an orange powder (0.0217 g, 45% yield). 1HNMR (300 MHz, CDCl3) δ: 8.09 (1H, d, J=8.05 Hz), 7.87 (2H, t, J=768 Hz), 7.57–7.41 (4H, m), 5.35 (2H, s), 4.16 (2H, s), 3.56 (3H, s), 3.54 (2H, t, J=6.33 Hz), 2.38 (2H, t, J=6.58 Hz) 1.91 (2H, t, J=6.22 Hz).
Sources & evidence
- ORD record
- ord-8628b421e73a4cefa2a823eb34d98a92
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109186B2
Reaction notes
Loading…