Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Methylurea | HCID 11719 | — |
| Reactant | Methanol, magnesium salt (2:1) | HCID 164537 | — |
| Reactant | HCID 53726727 | HCID 53726727 | — |
| Product | HCID 12044455 | HCID 12044455 | 62.4% |
Reaction Steps
A mixture of 3-cyclopentyl-2-phenyl-propionic acid ethyl ester (1.70 g, 7.06 mmol) and methyl urea (1.04 mg, 14.13 mmol) in a solution of magnesium methoxide in methanol (7.4 wt %, 130.3 mL, 21.18 mmol) was refluxed at 100° C. for 24 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 1-(3-cyclopentyl-2-phenyl-propionyl)-3-methyl-urea (1.21 mg, 62.4%) as a white solid: mp 145-147° C.; EI-HRMS m/e calcd for C16H22N2O2 (M+) 274.1681, found 274.1682.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06528543B1 |
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| Source dataset | uspto-grants-2003_03 |
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| ORD ID | ord-ea76db2d934d48f385f8817fc8f2815a |
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| Source note | uspto-grants-2003_03 |
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