Reaction #657301

Reaction equation

Compound 6

1-{[2-(Hex-5-enylmethylcarbamoyl)-4-hydroxycyclopentane carbonyl]amino}-2-vinylcyclopropane carboxylic acid ethyl ester

LiOH

HCl

→

compound 7

Yield 90.0%

1-{[2-(Hex-5-enylmethylcarbamoyl)-4-hydroxycyclopentane-carbonyl]amino}-2-vinylcyclopropanecarboxylic acid

Yield 90.0%

Solvents

DMF

Conditions

Workup

1. 1
   Othertransferred to a 20 mL microwave reaction vessel
2. 2
   OtherThe reaction vessel was sealed
3. 3
   OtherThe reaction was irradiated for 30 min to 130° C
4. 4
   Extractionextracted 3 times with EtOAc (20 mL)
5. 5
   WashThe pooled organic layers were washed with brine
6. 6
   Dryingdried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   OtherThe solvent was evaporated in vacuo

Procedure

Compound 6 (493 mg, 1.21 mmol) was dissolved in DMF (1 mL) and transferred to a 20 mL microwave reaction vessel. Then, aqueous LiOH (2 M, 10.5 mL) and a stirbar were added. The reaction vessel was sealed and the immiscible slurry was shaken vigorously before insertion in the microwave cavity. The reaction was irradiated for 30 min to 130° C. The reaction mixture was cooled to 40° C. and the clear solution acidified to pH 2 with aqueous HCl (1 M, 24 mL) and extracted 3 times with EtOAc (20 mL). The pooled organic layers were washed with brine, dried (MgSO4) and filtered. The solvent was evaporated in vacuo to afford compound 7 (410 mg, 90%). LC/MS (Method A): tR=2.46 min, >95%, m/z (ESI+)=379 (MH+).

Source