2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methanesulfinyl-benzyl)-N-methoxy-acetamide → HCID 86592766, compound
Reaction equation
C[C:2]1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[S:21]([CH3:23])=[O:22])[O:11][CH3:12])=[O:9])[C:4](=[O:24])[O:3]1>CO>[CH3:2][O:3][C:4](=[O:24])[C:5]([OH:6])=[CH:7][C:8](=[O:9])[N:10]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[S:21]([CH3:23])=[O:22])[O:11][CH3:12]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methanesulfinyl-benzyl)-N-methoxy-acetamide was reacted with methanol using the procedure described for the synthesis of compound 90-C to yield 3-[(4-fluoro-2-methanesulfinyl-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester as a white sticky solid (0.1020 g, 100% yield). This crude was reacted with paraformaldehyde and 4-amino-butyric acid using the procedure described for Compound 810 to give the title compound as an orange solid (0.0360 g, 64% yield). 1HNMR (300 MHz, CDCl3) δ: 7.75 (1H, dd, J=8.05, 2.56 Hz), 7.48 (1H, dd, J=8.42, 4.76 Hz), 7.21 (1H, td, J=8.05, 2.56 Hz), 4.96 (2H, q), 4.19 (2H, s), 3.78 (3H, s), 3.58 (2H, td, J=6.95, 1.83 Hz), 2.82 (3H, s), 2.39 (2H, t, J=6.95 Hz), 1.97–1.92 (2H, m).
Sources & evidence
- ORD record
- ord-24de35a415b943d29e9a338a675308b5
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109186B2
Reaction notes
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