Triphenylphosphine → methyl 4-[3-[(E)-(1-benzylindol-3-yl)methylideneamino]oxypropoxy]-2-[(4-tert-butylbenzoyl)amino]benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-tert-butyl-benzoylamino)-4-hydroxy-benzoic acid methyl ester (0.313 g, 0.96 mmol) in tetrahydrofuran (14 mL) was added 1-benzyl-1H-indole-3-carbaldehyde O-(3-hydroxy-propyl)-oxime (0.303 g, 0.98 mmol) and triphenyl phosphine (0.327 g, 1.26 mmol). The reaction was cooled to 0° C., diisopropyl azodicarboxylate (0.240 mL, 1.22 mmol) was added and warmed to room temperature overnight. It was poured into brine and extracted with ethyl acetate. The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (10/90) to afford 4-[3-({[(1E)-(1-benzyl-1H-indol-3-yl)methylidene]amino}oxy)-propoxy]-2-[(4-tert-butylbenzoyl)amino]benzoic acid methyl ester (0.328g, 55 %) as a white solid. (+ES, M+H) m/z 618. 1H NMR (400 MHz, DMSO-d6); δ 11.95 (s, 1H), 8.42 (d, 1H), 8.38 (s, 1H), 7.98 (m, 2H), 7.88 (d, 2H), 7.82 (s, 1H) 7.62 (d, 2H), 7.47 (d, 1H), 7.29 (m, 2H), 7.21 (m, 4H), 7.08 (m, 1H), 6.81 (dd, 1H), 5.43 (s, 2H), 4.24 (m, 4H), 3.88 (s, 3H), 2.19 (m, 2H), 1.32 (s, 9H). Elemental analysis: Calcd. for C38H39N3O5: C, 73.88; H, 6.36; N, 6.8. Found: C, 73.40; H, 6.44; N, 6.37.

Provenance & Evidence