Glycine tert-butyl ester hydrochloride → HCID 178444050, compound

Participants

Reaction Steps

To a stirred solution of 2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazole-5-carbaldehyde INT-47 (571 mg, 1.63 mmol) in DCM (6 mL) was added tert-butyl 2-aminoacetate hydrochloride (328 mg, 1.96 mmol). After 1 h, sodium triacetoxyhydroborate (691 mg, 3.26 mmol) was added. After stirring at room temperature for 18 h, the reaction mixture was quenched with NaHCO3 (10 mL), stirred for 10 min and split through a hydrophobic frit and evaporated. The crude product was purified by column chromatography (MeOH/EA) to give 228 mg (30%) of tert-butyl 2-(((2-(4-(heptyloxy)benzyl)-1H-benzo[d]imidazol-5-yl)methyl)amino)acetate INT-48 as a pale yellow oil. LCMS-ESI (m/z) calculated for C28H39N3O3: 465; found 466 [M+H]+, tR=1.17 min (Method 3).

Provenance & Evidence