Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N-(tert-butoxycarbonyl)glycine | HCID 78288 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | HCID 59191369 | HCID 59191369 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59191328 | HCID 59191328 | 58% |
Reaction Steps
To a solution of 1-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluorophenyl]ethanone (0.37 mmol; 100 mg) in dry THF (2 mL) cooled to 0° C. were added, N-Boc-glycine (0.37 mmol; 64 mg), benzotriazol-1-yloxytris(dimethylamino)phosphoniumhexafluoro phosphate (0.37 mmol; 190 mg) and triethylamine (1.09 mmol; 153 μL). The reaction was stirred at 0° C. for 3 hours and overnight at room temperature. The mixture was concentrated, treated with saturated NH4Cl and extracted with dichloromethane. Combined organic phases were washed with water, dried over Na2SO4 and concentrated in vacuo. The title compound (91 mg; 58%) was obtained as clear oil after purification on preparative TLC (cyclohexane/ethyl acetate: 7/3).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09309179B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-75a37744e68c4af489b784cd159c7311 |
|---|
| Source note | uspto-grants-2016_04 |
|---|