Acetic Acid → HCID 22318856, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of {(3-tert-Butoxycarbonylamino-propionyl)-[2-(4-nitro-phenyl)-ethyl]-amino}-acetic acid tert-butyl ester (2.5 mmol) in 11 mL THF is 22 mL water added, followed by NaOH (17.5 mmol). After heating at 60° C. for 5½ hours it is quenched with acetic acid (20 mmol). It is placed in the refrigerator for 2% days. The THF is evaporated off, and the remaining water is extracted several times with EtOAc. The organic layers are combined, dried over Na2SO4 and evaporated in vacuo yielding {(3-tert-Butoxycarbonylamino-propionyl)-[2-(4-nitro-phenyl)-ethyl]-amino}-acetic acid, 983 mg, as a dark yellow/brown oil/foam (99%): 1H NMR (CD3OD) 1.40 (d, 9H), 2.44-2.45 (m, 2H), [2.98, 3.03](t, 2H), 3.22-3.30 (m, 2H), [3.60, 3.65](t, 2H), 4.06 (s, 2H), [7.52, 7.54](d, 2h), 8.16 (t, 2H); LRMS calcd 395.42, found [M−H] 394.0.

Provenance & Evidence