HuagongsheHuagongshe Chemistry Print Report · For research reference only
Gamma-Aminobutyric Acid → 4-{4-[(4-Fluoro-2-methylsulfanyl-benzyl)-methyl-carbamoyl]-3-hydroxy-2-oxo-2,5-dihydro-pyrrol-1-yl}-butyric acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Gamma-Aminobutyric Acid | HCID 119 | — |
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | 2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methylsulfanyl-benzyl)-N-methyl-acetamide | HCID 69656323 | — |
| Product | 4-{4-[(4-Fluoro-2-methylsulfanyl-benzyl)-methyl-carbamoyl]-3-hydroxy-2-oxo-2,5-dihydro-pyrrol-1-yl}-butyric acid | HCID 54691789 | 49% |
Reaction Steps
2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-2-methylsulfanyl-benzyl)-N-methyl-acetamide was reacted with paraformaldehyde and 4-amino-butyric acid as described in Method 44B to give the title compound as a white solid (0.05 g, 49% yield). 1HNMR (300 MHz, CDCl3) δ: 7.11 (1H, dd, J=8.42, 5.85 Hz), 6.91 (1H, dd, J=9.52, 2.57 Hz), 6.82 (1H, td, J=8.41, 2.56 Hz), 4.64 (2H, s), 4.15 (2H, s), 3.55 (2H, t, J=6.96 Hz), 2.98 (3H, s), 2.47 (3H, s), 2.38 (2H, t, J=6.95 Hz), 1.96–1.88 (2H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07109186B2 |
| Source dataset | uspto-grants-2006_09 |
| ORD ID | ord-248297ce0bd0447782822b0cea0cef41 |
| Source note | uspto-grants-2006_09 |