Reaction #42690

Reaction equation

intermediate

tert-Butyl (2-((4-((((Z)-(((3-(4-(allyloxy)phenyl)-5-methyl-4-isoxazolyl)carbonyl)imino)((tert-butoxycarbonyl)amino)methyl)amino)methyl)-2,6-dichlorophenyl)amino)-2-oxoethyl)5-hexen-1-ylcarbamate

→

crude product

tert-Butyl (24E)-9-((tert-butoxycarbonyl)amino)-14,33-dichloro-5-methyl-7,17-dioxo-4,27-dioxa-3,8,10,16,19-pentaazatetracyclo[26.2.2.212,15.02,6]tetratriaconta-1(30),2,5,8,12,14,24,28,31,33-decaene-19-carboxylate

Solvents

1,2-dichloroethane

1,2-dichloroethane

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   OtherSolvent was evaporated in vacuo

Procedure

The intermediate (85 mg, 0.104 mmol) from Step 7(B) was dissolved in 27 mL of 1,2-dichloroethane, followed by the addition of Grubbs Catalyst 2nd Generation (6 mg, 0.007 mmol) with 1 mL of 1,2-dichloroethane. The resulting reaction mixture was stirred at 45° C. for 2 hrs. Solvent was evaporated in vacuo to give a crude product, which was purified by flash chromatography (8% EtOAc/DCM) to give two compounds, 8 mg of cis-8C (Rf 0.37) and 45 mg of trans-8C (Rf 0.26).

Source