반응 #712245

반응 방정식

LiOH hydrate

tert-butyl 6-(4-chlorophenyl)-5-oxo-4-azaspiro[2.4]heptane-4-carboxylate

→

3-(1-(tert-butoxycarbonylamino)cyclopropyl)-2-(4-chlorophenyl)propanoic acid

수율 86.2%

용매

water

MeOH

THF

반응 조건

후처리

1. 1
   기타The solvents were evaporated in vacuo
2. 2
   추출extracted with ether (2×)
3. 3
   추출extracted with EtOAc
4. 4
   세척The combined organic phases were washed with brine
5. 5
   기타dried
6. 6
   농축concentrated

실험 절차

A solution of LiOH hydrate (0.24 g, 5.7 mmol) in water (2 mL) was added to a stirred solution of tert-butyl 6-(4-chlorophenyl)-5-oxo-4-azaspiro[2.4]heptane-4-carboxylate (0.46 g, 1.4 mmol) in MeOH (2 mL) and THF (2 mL). The reaction was stirred at room temperature overnight. The solvents were evaporated in vacuo. The residue was taken up in water and extracted with ether (2×). The aqueous phase was acidified by 2N HCl and extracted with EtOAc. The combined organic phases were washed with brine, dried and concentrated to give 3-(1-(tert-butoxycarbonylamino)cyclopropyl)-2-(4-chlorophenyl)propanoic acid (0.41 g, 84%) as a white solid. LCMS (APCI+) [M-Boc+H]+ 240.0; Rf: 2.38 min.

출처