反応 #657303

反応方程式

LiOH

MeOH

Crude compound 26

14-(4-Methoxy-benzyl)-18-(4-nitro-benzoyloxy)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl ester

water

→

title compound

収率 67.0%

18-Hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo[14.3.0.0*4,6*]-nonadec-7-ene-4-carboxylic acid ethyl ester

収率 67.0%

溶媒

HOAc

THF

反応条件

後処理

1. 1
   その他the solution was evaporated
2. 2
   workup.ADDITIONWater was added
3. 3
   抽出the mixture was extracted with DCM (2×30 ml)
4. 4
   洗浄The pooled organic phase was washed with NaHCO3 (aq), water, brine
5. 5
   乾燥dried over MgSO4
6. 6
   その他The crude product was purified by column chromatography on silica (DCM/MeOH: 100/0-80/20)

実験手順

Crude compound 26 (445 mg) was dissolved in THF (20 ml), MeOH (10 ml) and water (10 ml). After cooling to 0° C. 1M LiOH (2 ml) was added. After 1.5 h the hydrolysis was completed and HOAc (1 ml) was added and the solution was evaporated to appr 10 ml. Water was added and the mixture was extracted with DCM (2×30 ml). The pooled organic phase was washed with NaHCO3 (aq), water, brine and dried over MgSO4. The crude product was purified by column chromatography on silica (DCM/MeOH: 100/0-80/20) to give the title compound (201 mg, 67%).

出典