Water → HCID 90036988, compound

Participants

Reaction Steps

DIEA (177 mg, 242 μl, 1.37 mmol, Eq: 5.00) was added to a mixture of (S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-9-carboxylic acid (180 mg, 274 μmol, Eq: 1.00), tert-butyl 3-aminopropanoate hydrochloride (49.8 mg, 274 μmol, Eq: 1.00), HBTU (104 mg, 274 μmol, Eq: 1.0) and HOBT.H2O (37.0 mg, 274 μmol, Eq: 1.0) in DMF (3.41 mL) at 0° C. and the mixture was warmed to RT. After 45 min. the mixture was diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to afford 3-({(S)-9-(6-bromo-2-methoxy-naphthalen-1-ylmethyl)-7-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene-4-carbonyl}-amino)-propionic acid tert-butyl ester (150 mg, 69%) as an off-white foam.

Provenance & Evidence