Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | pentafluorophenyl 3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetate | HCID 23512249 | — |
| Reactant | HCID 86587791 | HCID 86587791 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86595080 | HCID 86595080 | 69% |
Reaction Steps
To a stirred solution of pentafluorophenyl 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetate (459 mg, 0.96 mmol) and ethyl (R)-3-methoxy-4-(2-aminopropoxy)benzoate (242 mg, 0.96 mmol) in DMF (5 mL) was added Et3N (200 μl, 1.43 mmol), and the resulting mixture was stirred for 2 hr. The mixture was diluted with EtOAc, washed with 0.5 N HCl, brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica-gel with CHCl3—MeOH (50:1, v/v) as eluent to give 360 mg (69%) ethyl (R)-3-methoxy-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate as a colorless crystalline solid. 1H-NMR (CDCl3) δ1.23-1.28 (m, 3 H), 1.38-1.41 (t, 3 H, J=7.3 Hz), 2.32 (s, 3 H), 3.50-4.13 (m, total 11 H), 4.36 (q, 2 H, J=7.3 Hz), 6.65-8.13 (series of m, total 12 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06756378B2 |
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| Source dataset | uspto-grants-2004_06 |
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| ORD ID | ord-4ea534b3c89c49279538212a1eaba2be |
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| Source note | uspto-grants-2004_06 |
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