HCID 178458084, compound → HCID 178461774, compound
Reaction equation
[NH2:1][C:2](=[O:27])[CH:3]([CH3:26])[C@H:4]([NH:18]C(=O)OC(C)(C)C)[C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:13][C:7]=2[N:6]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:18][C@H:4]([C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([C:14]([CH3:15])([CH3:17])[CH3:16])=[CH:13][C:7]=2[N:6]=1)[C@@H:3]([CH3:26])[C:2]([NH2:1])=[O:27]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of tert-butyl [(1S)-3-amino-1-(5-tert-butyl-1H-benzimidazol-2-yl)-2-methyl-3-oxopropyl]carbamate (Preparation 29, 3.07 g, 8.2 mmol) in DCM (50 mL) and TFA (10 mL) was stirred at room temperature for 3 hours before concentrating in vacuo. Saturated aqueous NaHCO3 solution (100 mL) was added and the product extracted with 2-MeTHF (4×100 mL). The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified using reverse phase column chromatography eluting with 0-40% acetonitrile in water. The resulting solid was dissolved in MeCN (40 mL) at 50° C. and methanol added before allowing the solution to cool. The resulting white precipitate was collected, dried, and further triturated with EtOAc (5 mL) twice to afford a white solid as the desired (2R,3S) diastereomer.