Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Methylurea | HCID 11719 | — |
| Reactant | Methanol, magnesium salt (2:1) | HCID 164537 | — |
| Reactant | HCID 54098154 | HCID 54098154 | — |
| Product | HCID 12044452 | HCID 12044452 | 9.4% |
Reaction Steps
A mixture of 3-cyclopentyl-2-(3,4-difluoro-phenyl)-propionic acid methyl ester (1.65 g, 6.14 mmol) and methyl urea (683 mg, 9.22 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 16.6 mL, 12.3 mmol) was refluxed at 100° C. for 8 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2-(3,4-difluoro-phenyl)-propionyl]-3-methyl-urea (180 mg, 9.4%) as a white solid: mp 111-113° C.; EI-HRMS m/e calcd for C16H20F2N2O2 (M+) 310.1493, found 310.1499.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06528543B1 |
|---|
| Source dataset | uspto-grants-2003_03 |
|---|
| ORD ID | ord-5523b8d9a40c4d1382d5cc78f6cb2e65 |
|---|
| Source note | uspto-grants-2003_03 |
|---|