Reacción #48301

Ecuación de reacción

HCl

LiOH

(S)-Methyl 2-(tert-butoxycarbonyl)-3-(4-(trifluoromethyl)phenyl)propanoate

→

(S)-2-(tert-butoxycarbonyl)-3-(4-(trifluoromethyl)phenyl)propanoic acid

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe aqueous layer was washed with diethyl ether
2. 2
   Extracciónthe organics were back extracted with 1% aqueous sodium bicarbonate
3. 3
   Extracciónextracted with EtOAc
4. 4
   LavadoThe combined organic layers were washed with brine
5. 5
   Secadodried over sodium sulfate
6. 6
   Concentraciónconcentrated

Procedimiento

(S)-Methyl 2-(tert-butoxycarbonyl)-3-(4-(trifluoromethyl)phenyl)propanoate (6.20 g, 17.9 mmol) was dissolved in THF (180 mL) and cooled to 0° C. A 0.2 M of aq. LiOH (89.3 ml, 17.9 mmol) was added dropwise and stirred 20 minutes before TLC analysis (2:1 Hexanes/EtOAc) showed no starting material. The PH of the reaction was carefully adjusted to PH=8 with 1 N HCl. The aqueous layer was washed with diethyl ether and the organics were back extracted with 1% aqueous sodium bicarbonate and the combined aqueous layers were carefully brought to a PH =4 and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to afford (S)-2-(tert-butoxycarbonyl)-3-(4-(trifluoromethyl)phenyl)propanoic acid, which was used without further purification.

Fuente