Reaction #657303

Reaction equation

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

Yield 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

Yield 67.0%

Solvents

HOAc

THF

Conditions

Workup

1. 1
   Otherthe solution was evaporated
2. 2
   workup.ADDITIONWater was added
3. 3
   Extractionthe mixture was extracted with DCM (2×30 ml)
4. 4
   WashThe pooled organic phase was washed with NaHCO3 (aq), water, brine
5. 5
   Dryingdried over MgSO4
6. 6
   OtherThe crude product was purified by column chromatography on silica (DCM/MeOH: 100/0-80/20)

Procedure

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%).

Source