反応 #712257

反応方程式

Sodium chlorite

tert-Butyl 1-(1-(4-chlorophenyl)-2-oxoethyl)cyclopropylcarbamate

2-methyl-2-butene

KH2PO4

citric acid

→

2-(1-(tert-butoxycarbonylamino)cyclopropyl)-2-(4-chlorophenyl)acetic acid

収率 91.1%

溶媒

t-BuOH

water

反応条件

後処理

1. 1
   抽出The reaction was extracted with EtOAc
2. 2
   洗浄The combined organic layers were washed with brine
3. 3
   その他dried
4. 4
   濃縮concentrated

実験手順

tert-Butyl 1-(1-(4-chlorophenyl)-2-oxoethyl)cyclopropylcarbamate (0.64 mmol), 2-methyl-2-butene (1.6 mL, 2.0 M THF solution, 3.2 mmol) and KH2PO4 (0.087 g, 0.64 mmol) were dissolved in t-BuOH (20 mL)-water (6 mL). Sodium chlorite (0.174 g, 1.93 mmol) was added portionwise at 0° C. The mixture was stirred at room temperature for 2 hours and then acidified with 10% citric acid. The reaction was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated to give 2-(1-(tert-butoxycarbonylamino)cyclopropyl)-2-(4-chlorophenyl)acetic acid (0.19 g, 91%) as a colorless syrup, which was used for amide coupling without further purification. LCMS: 325.8 [M+H+] (APCI+); Rf: 3.31 min.

出典