2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methanesulfonyl-benzyl)-N-methoxy-acetamide → 3-[(4-Fluoro-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester
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]=2S(C)(=O)=O)[O:11][CH3:12])=[O:9])[C:4](=[O:25])[O:3]1>CO>[CH3:2][O:3][C:4](=[O:25])[C:5]([OH:6])=[CH:7][C:8](=[O:9])[N:10]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)[O:11][CH3:12]Participants
3
Procedure
2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methanesulfonyl-benzyl)-N-methoxy-acetamide was reacted with methanol using the procedure described for the synthesis of compound 90-C to yield 3-[(4-fluoro-benzyl)-methoxy-carbamoyl]-2-hydroxy-acrylic acid methyl ester as a white sticky solid (0.102 g, 100% yield). This 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 (0.018 g, 14% yield). 1HNMR (300 MHz, CDCl3) δ: 7.78 (1H, dd, J=8.05, 2.56 Hz), 7.59–7.54 (1H, m), 7.36–7.29 (1H, m), 5.35 (2H, s), 4.25 (2H, s), 3.83 (3H, s), 3.60 (2H, t, J=6.95 Hz), 3.22 (3H, s), 2.43 (2H, t, J=6.95 Hz), 2.00–1.96 (2H, m).
Sources & evidence
- ORD record
- ord-c291e0de6ee447f08e572edf1b13e689
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109186B2
Reaction notes
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