Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 86603173 | HCID 86603173 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86603186 | HCID 86603186 | — |
Reaction Steps
A mixture of {2-[3-(3-trifluoromethyl-phenyl)-ureido]-thiazol-5-yl}-acetic acid methyl ester (4.17 mmol), paraformaldehyde (0.95 equiv.) and K2CO3 (0.95 equiv.) in DMSO (10.0 mL) was heated at 50° C. for 1.5 hours. The reaction was cooled, diluted with EtOAc, washed with water, dried and concentrated to give a residue that was purified by flash column chromatography on silica gel (0 to 6% MeOH in EtOAc) to provide 3-hydroxy-2-{2-[3-(3-trifluoromethyl-phenyl)-ureido]-thiazol-5-yl}-propionic acid methyl ester (compound 73.1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07601725B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-845eb9ae972f45a89024cb246503f64c |
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| Source note | uspto-grants-2009_10 |
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