HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Bromo-4-fluorobenzonitrile | HCID 118939 | — |
| Reactant | O-benzyl-D-serinamide | HCID 58987402 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide | HCID 67509048 | 17.6% |
Reaction Steps
A solution of 2-bromo-4-fluorobenzonitrile (200 mg, 1.00 mmol), O-benzyl-D-serinamide (290 mg, 1.49 mmol) and DIEA (0.466 mL, 2.68 mmol) in DMSO (3 mL) was stirred at 100 C for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 0-60% EtOAc in hexane to give (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide (66 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359375B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-7b1a324529b0441bba81e652b653dea6 |
| Source note | uspto-grants-2016_06 |