HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-[4-(2-Amino-1,3-oxazol-4-yl)phenyl]cyclopropanecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Urea | HCID 1176 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate | HCID 86602275 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | MeOH tetrahydrofuran | HCID 21899815 | — |
| Product | 1-[4-(2-Amino-1,3-oxazol-4-yl)phenyl]cyclopropanecarboxylic acid | HCID 66661651 | — |
Reaction Steps
A mixture of methyl 1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate (0.20 g, 0.00079 mol, example 243, steps 1 & 2) and urea (0.095 g, 0.0016 mol) in ethanol (5.0 mL, 0.086 mol) was refluxed overnight. The mixture was diluted with ethyl acetate and washed with sat'd. NaHCO3, brine, dried and concentrated. The methyl ester was purified by CombiFlash using CH2Cl2/EtOAc (max. EtOAc 100%). The ester was hydrolysized using lithium hydroxide (6.0 eq.) in methanol/THF and then acidified by adding 1 N HCl. The solvent was removed under vacuum and the crude product was used in the next step. LC-MS: 259.2 (M+H+) methyl eater; 245.2 (M+H+) acid
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07304081B2 |
| Source dataset | uspto-grants-2007_12 |
| ORD ID | ord-0c8a61af6a054b3181a4e0be40fca4c5 |
| Source note | uspto-grants-2007_12 |