Dicyclohexylcarbodiimide → Boc-L-phenylalaninamide

Temperature

0 °C

Dicyclohexylcarbodiimide (348 mg, 1.69 mmol) was added to a chilled solution of Boc-L-phenylalanine (387 mg, 1.46 mmol) and the ammonium salt of 1-hydroxybenzotriazole (248 mg, 1.63 mmol) in DMF (5 ml). The solution was stirred at 0° C. for 90 min, then at room temperature for 2 h. The reaction mixture was filtered, and the filtrate poured into water (77 ml). The emulsion was extracted with diethylether (1×200 ml), the layers separated, and the organic phase washed with 5% NaHCO3, water and brine, then dried (sodium sulphate) , filtered, and the filtrate concentrated in vacuo to give Boc-L-phenylalanine amide (370 mg, 96%). Analytical HPLC in the condition of example 1a), using a linear gradient of 20% A to 80% A over 25 min, then 80% A for 10 min, showed a single peak at 14.92 min.

1. waitat room temperature for 2 h
2. filtrationThe reaction mixture was filtered
3. additionthe filtrate poured into water (77 ml)
4. extractionThe emulsion was extracted with diethylether (1×200 ml)
5. customthe layers separated
6. washthe organic phase washed with 5% NaHCO3, water and brine
7. dry with materialdried (sodium sulphate)
8. filtrationfiltered
9. concentrationthe filtrate concentrated in vacuo

ORD record

ord-7c5254c3b8144d9fb8d646cc2ab57ca6

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05760248