Reacción #67654

Ecuación de reacción

product

N-[(2R)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-N-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]amine

triethylamine

9-fluorenylmethyl chloroformate

→

N-[(2R)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-N-[(2S)-2-(tert-butoxycarbonylamino)-3-phenylpropyl]-N-[9-fluorenylmethoxycarbonyl]amine

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthe mixture was concentrated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate (10 mL)
3. 3
   Lavadowash with 10% NaHCO3 (2×10 mL), 10% citric acid (2×10 mL), brine (10 mL)
4. 4
   Secadodried over sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónthe filtrate was concentrated
7. 7
   OtroThe residue was purified by flash column chromatography on silica gel eluting with chloroform (1.68 g, 90%)

Procedimiento

The product from Example 26B (1.28 g, 2.6 mmol) in tetrahydrofuran (11 mL) was treated with triethylamine (0.39 mL, 2.8 mmol) and 9-fluorenylmethyl chloroformate (0.72 g, 2.8 mmol) at ambient temperature. After stirring for 1 hour, the mixture was concentrated and the residue was dissolved in ethyl acetate (10 mL), wash with 10% NaHCO3 (2×10 mL), 10% citric acid (2×10 mL), brine (10 mL), dried over sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by flash column chromatography on silica gel eluting with chloroform (1.68 g, 90%). 1H NMR (CDCl3) δ 7.82-6.94 (m, 18H), 4.93 (br s, 1H), 4.66-4.43 (m, 2H), 4.20 (t, 1H), 3.87-3.35 (m, 4H), 3.00-2.20 (m, 7H), 1.38-1.23 (m, 18H); MS (ESI+) m/z 706 (M+H)+.

Fuente