Reacción #502129

Ecuación de reacción

Example 45b

2-((tert-Butoxy)-N-methylcarbonylamino)ethyl(2S)-2-(6-methoxy(2 naphthyl))propanoate

TFA

→

product

2-(Methylamino)ethyl(2S)-2-(6-methoxy(2-naphthyl))propanoate

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe ice bath was removed
2. 2
   Otrowas evaporated
3. 3
   workup.ADDITIONThe residue was treated with aqueous sodium carbonate (10%)
4. 4
   Extracciónextracted with EtOAc
5. 5
   LavadoThe combined organic extracts were washed with water, brine
6. 6
   Secadodried over sodium sulfate
7. 7
   Otrothe solvent was evaporated

Procedimiento

The product of the Example 45b (17.1 g, 50 mmol) was dissolved in CH2Cl2 (400 mL). The solution was cooled to 0° C. and TFA (80 mL) was added drop-wise. The ice bath was removed and the reaction mixture was stirred at room temperature overnight, then the solvent. was evaporated. The residue was treated with aqueous sodium carbonate (10%) and extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over sodium sulfate, and the solvent was evaporated. Trituration of the resulting solid with hexane gave the pure product as a white solid. Mp 64-68° C. 1HNMR (300 MHz, CDCl3) δ 7.67 (d, J=8.5 Hz, 2H), 7.66 (d, J=1.3, 1H), 7.4 (dd, J=8.5 and 1.8 Hz, 1H), 7.18-7.08 (m, 2H), 4.18 (t, J=5.4 Hz, 2H), 3.89 (s, 3H), 3.80 (q, J=7.1 Hz, 1H), 2.73 (t, J=5.4 Hz, 2H), 2.31 (s, 3H), 1.56 (d,l J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 174.5, 157.6, 135.6, 133.6, 129.2, 128.8, 127.1, 126.1, 125.8, 118.9, 105.5, 63.9, 55.2, 50.0, 45.3, 36.0, 18.4.

Fuente