1,2-Dichloroethane → 3(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-hydroxybutyric Acid tert-Butyl Ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of compound 704 (318 mg, 0.86 mmol) and compound 707 (370 mg, 0.78 mmol) in 1:1 CH2Cl2 :DMF (8.0 mL) was added bis(triphenylphosphine) palladium dichloride (10 mg), followed by the dropwise addition of tri-n-butyl tin hydride (320 μL, 1.19 mmol). After the addition was complete, HOBT (212 mg, 1.57 mmol) was added and the reaction was cooled to 0° C. added EDC (180 mg, 0.94 mmol) was added and the reaction allowed to warm to rt and stir overnight. The reaction was concentrated in vacuo and the residue taken up into EtOAc and sat. aq. KHSO4. The layers were separated and the organic phase was washed with sat. aq. K2CO3, brine, dried over MgSO4, filtered and concentrated in vacuo. Chromatography on silica gel (elution with 2% MeOH:CH2Cl2) provided 150 mg of compound 708. ##STR87##

Provenance & Evidence