Reaction SMILES: C([O:5][C:6](=[O:41])[C:7]([CH2:38][CH:39]=[CH2:40])([CH:11]([C:16](=[O:37])[NH:17][CH:18]1[C:24](=[O:25])[N:23]([CH3:26])[C:22]2[CH:27]=[CH:28][CH:29]=[CH:30][C:21]=2[C:20]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:19]1)[CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:8][CH:9]=[CH2:10])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:8]([C:7]([CH:11]([C:16](=[O:37])[NH:17][CH:18]1[C:24](=[O:25])[N:23]([CH3:26])[C:22]2[CH:27]=[CH:28][CH:29]=[CH:30][C:21]=2[C:20]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:19]1)[CH2:12][CH:13]([CH3:15])[CH3:14])([CH2:38][CH:39]=[CH2:40])[C:6]([OH:41])=[O:5])[CH:9]=[CH2:10]
Reactant: C=CCC(CC=C)(C(=O)OC(C)(C)C)C(CC(C)C)C(=O)NC1N=C(c2ccccc2)c2ccccc2N(C)C1=O
Solvent: ClCCl
Solvent: O=C(O)C(F)(F)F
Product: C=CCC(CC=C)(C(=O)O)C(CC(C)C)C(=O)NC1N=C(c2ccccc2)c2ccccc2N(C)C1=O
Yield: 92.3 %

Procedure:
A solution of compound 29 (300 mg, 0.54 mmol) in 50 ml TFA/CH2Cl2 (1:1) was stirred for 2 hr at ambient temperature, then concentrated under vacuum. Two cycles of toluene addition and removal of volatiles gave 250 mg of 30 as a white solid (92%) which was used in the next step without purification. ESI ES+=502.3 (M+1) Step 3: Preparation of 2,2-Diallyl-3-isobutyl-N4-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-succinamide 31. To a solution of 30 (250 mg, 0.5 mmol) in 30 ml DMF was added HATU (250 mg, 0.66 mmol) and DIEA (400 uL, 2.2 mmol). After stirring for 2 hrs, ammonia gas was bubbled into the solution for 5 minutes using a glass inlet tube. The mixture was then stirred at ambient temperature overnight. Water was added (10 mL) and the solvent was removed under vacuum to give a yellow oil which was taken up in ethyl acetate and water (1:1). The organic layer was washed twice with water and then brine, and dried over Na2SO4. After filtration and concentration, the crude product was purified using silica gel chromatography (CH2Cl2/methanol 10:0.5) to give compound 31 (120 mg) as a white solid (48%). 1H NMR (CDCl3) 0.95-0.88 (dd, 6H), 1.32-1.28 (m, 1H), 1.64-1.50 (m, 1H), 1.90-1.80 (m, 1H), 2.35-2.00 (m, 1H), 2.80-2.54 (m, 4H), 3.48 (s, 3H), 5.38-5.14 (m, 5H), 5.54-5.51 (d, 1H), 5.90-5.78 (m, 2H), 7.65-7.25 (m, 9H), 8.52 (s, 1H). ESI ES+=523.2 (M+Na). Step 4: Preparation of 1-[(1R)-3-methyl-1-[1,3-dihydro-1-methyl-2-oxo-5-phenyl-2H-1,4-benzodiazepin-3-ylcarbamoyl]-butyl]-cyclopent-3-enecarboxylic amide 32. To a solution of 31 (110 mg, 0.22 mmol) in 20 ml of toluene and CH2Cl2 (1:1) at 100 degree was added (bis(tricyclohexylphosphine)-benzylidine ruthenium (IV) dichloride) (24 mg, 0.029 mmol). The mixture was stirred at 100 degree for 4 hrs and another 24 mg Grubbs' catalyst was added. The mixture was then stirred at 100 degree for another 4 hrs. Then the solution was cooled to RT, after which 100 mg of charcoal was added. The mixture was filtered through celite to provide a slightly yellow solution, then concentrated. The residue was purified in silica gel chromatography with CH2Cl2/methanol (10:0.5) to give 48 mg of 32 (46%). 1H NMR (CDCl3) 0.97-0.90 (dd, 6H), 1.30-1.25 (m, 1H), 1.65-1.57 (m, 1H), 2.00-1.85 (m, 1H), 2.40-2.30 (d, 1H), 2.80-2.65 (m, 2H), 3.00-2.80 (d, 1H), 3.40-3.20 (m, 1H), 3.47 (s, 3H), 5.40-5.20 (s, 1H), 5.52-5.49 (d, 1H), 5.80-5.71 (m, 2H), 7.63-7.20 (m, 9H), 7.90 (s, 1H). API AP+ 473.1 (M+1).