Reaction equation
ClC1C=C(C=CC=1Cl)CN(C)C(=O)C=C1C(=O)OC(C)(C)O1.C=O.NCCC(N)=O.[Cl:31][C:32]1[CH:33]=[C:34]([CH:57]=[CH:58][C:59]=1[Cl:60])[CH2:35][N:36]([CH3:56])[C:37]([C:39]1[CH2:43][N:42]([CH2:44][CH2:45][C:46]([NH:48]CCC(O)=O)=[O:47])[C:41](=[O:54])[C:40]=1[OH:55])=[O:38]>>[Cl:31][C:32]1[CH:33]=[C:34]([CH:57]=[CH:58][C:59]=1[Cl:60])[CH2:35][N:36]([CH3:56])[C:37]([C:39]1[CH2:43][N:42]([CH2:44][CH2:45][C:46](=[O:47])[NH2:48])[C:41](=[O:54])[C:40]=1[OH:55])=[O:38]Participants
5
Reactant 4
Product 1
Procedure
N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide (Compound 37-A) was treated with paraformaldehyde and β-alaninamide as described in the preparation of Compound 37. The title compound was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA) to yield the title compound as an amber powder (0.0158 g, 7% yield). 1H NMR (300 MHz, CDCl3) δ: 2.68 (t, J=5.9 Hz, 2H), 3.02 (s, 3H), 3.79 (d, J=5.9 Hz, 2H), 4.29 (s, 2H), 4.58 (s, 2H), 6.23 (s, 1H), 6.59 (s, 1H), 7.09 (dd, J=8.4 Hz, J=10.3 Hz, 1H), 7.34 (d, J=1.8 Hz, 1H), 7.42 (d, J=8.4 Hz, 1H). HRMS (M−H) calcd for C16H17N3Cl2O4: 384.05179. found: 384.0517.
Workup
- customThe title compound was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA)
Sources & evidence
- ORD record
- ord-29fba2b605f04cc98e61c445564376f8
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109186B2
Linked notes
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