HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → (R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Bromo-4-fluorobenzonitrile | HCID 118939 | — |
| Reactant | (R)-2-Amino-4-methylpentanamide hydrochloride | HCID 56776963 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | (R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamide | HCID 67509372 | 60.3% |
Reaction Steps
A solution of 2-bromo-4-fluorobenzonitrile (200 mg, 1.00 mmol), D-leucine amide hydrochloride (200 mg, 1.20 mmol) and DIEA (0.620 mL, 3.56 mmol) in DMSO (3 mL) was stirred at 100 C for 18 h. EtOAc and water were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted first with 30% EtOAc in hexane, then with 80% EtOAc to give (R)-2-(3-bromo-4-cyanophenylamino)-4-methylpentanamide (187 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846928B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-edd233d2d9d94267b1ccbb0294686228 |
| Source note | uspto-grants-2014_09 |