Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | O-benzylglycine toluene-p-sulphonate | HCID 6451311 | — |
| Reactant | 2-((tert-Butoxycarbonyl)amino)-5-(trifluoromethyl)benzoic acid | HCID 15033886 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Benzyl acetate | HCID 8785 | 215.4% |
Reaction Steps
Glycine benzyl ester p-toluenesulfonate salt (6.03 g) was dissolved in DMF prior to the addition of Hunig's base (12.4 mL) and 2-(tert-butoxycarbonyl)amino-5-trifluoromethylbenzoic acid (6 g) (Takagishi et al., Synlett 1992, 360). After cooling to 0° C., BOP Reagent (8.69 g) was added. The resulting mixture was warmed to rt and was stirred 96 h. EtOAc was added along with 1 N HCl solution. The EtOAc layer was washed with 1 N HCl (aq), NaHCO3 solution (aq), and brine. The EtOAc was dried (MgSO4), filtered, and concentrated. Flash chromatography of the resulting residue gave 2-tert-butoxycarbonylamino-5-trifluoromethyl-benzoylamino)-acetic acid benzyl ester (5.78 g). MS found: (M+Na)+=475.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07087604B2 |
|---|
| Source dataset | uspto-grants-2006_08 |
|---|
| ORD ID | ord-0224c20f2e144680a90e3f6f2a7fd373 |
|---|
| Source note | uspto-grants-2006_08 |
|---|
