반응 #712220

반응 방정식

Lithium hydroxide hydrate

tert-butyl 4-(4-chlorophenyl)-2,2-dimethyl-5-oxopyrrolidine-1-carboxylate

→

4-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)-4-methylpentanoic acid

수율 63.2%

용매

THF MeOH H2O

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   세척washed with EtOAc (100 mL)
3. 3
   추출extracted into EtOAc (2×200 mL)
4. 4
   건조The product was dried over Na2SO4
5. 5
   농축concentrated in vacuo
6. 6
   기타The residual HCl was removed
7. 7
   기타by evaporating from toluene

실험 절차

Lithium hydroxide hydrate (6.44 ml, 232 mmol) was added to a stirred solution of tert-butyl 4-(4-chlorophenyl)-2,2-dimethyl-5-oxopyrrolidine-1-carboxylate (7.5 g, 23.2 mmol) in THF/MeOH/H2O (30 mL/30 mL/30 mL) at room temperature. The reaction mixture was stirred overnight and then concentrated in vacuo. The reaction mixture was taken up into water (200 mL), washed with EtOAc (100 mL), acidified with concentrated HCl and extracted into EtOAc (2×200 mL). The product was dried over Na2SO4 and concentrated in vacuo. The residual HCl was removed by evaporating from toluene to give 4-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)-4-methylpentanoic acid (5.0 g, 63.2% yield) as a white solid. LCMS (APCI+) [M-Boc+H]+ 242.0; Rt: 2.8 min.

출처