Methyl 4-aminobenzoate → Tert-butyl 2-(4-(cyclopentanecarboxamido)benzamido)-3-(4-hydroxy-3-methoxyphenyl)propanoate

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Reaction Steps

Prepared using General Procedures 5, 12 and 6 starting from methyl 4-aminobenzoate and using cyclopentane carbonyl chloride and tert-butyl 2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoate. LCMS-ESI (m/z) calculated for C27H34N2O6: 482. Found 505, [M+Na]+, tR=3.21 min (Method 1). 1H NMR (400 MHz, CDCl3) δ 7.79-7.67 (m, 2H), 7.60 (d, J=8.7 Hz, 2H), 6.88-6.75 (m, 1H), 6.73-6.60 (m, 2H), 6.56 (d, J=7.4 Hz, 1H), 5.52 (s, 1H), 4.89 (ddd, J=7.3, 6.1, 5.0 Hz, 1H), 3.76 (s, 3H), 3.16 (m, 2H), 2.69 (m, 1H), 2.01-1.85 (m, 4H), 1.80 (m, 2H), 1.69-1.58 (m, 2H), 1.46 (s, 9H).

Provenance & Evidence