CBZ-1-AMINO-1-CYCLOBUTANECARBOXYLIC ACID synthesis

Yield:-

Reaction Conditions:

with triethylamine;HATU in N,N-dimethyl-formamide at 20; for 2.5 h;Inert atmosphere;

Steps:

Step 1: To a stirred solution of10 1-{[(benzyloxy)carbonyl]amino }cyclobutanecarboxylic acid (2.0 g, 8.02 mmol), HATU (4.58 g,12.04 mmol) and triethylamine (5.59 mL, 40.1 mmol) in DMF (35 mL) under nitrogen wasadded N,O-dimethylhydroxylamine hydrochloride (1.565 g, 16.05 mmol). The reactionsuspension was stirred at room temperature for 2.5 h after which the reaction was diluted withethyl acetate (200 mL) and water. The organic layer was washed with water (2 x 100 mL) and15 brine, and was dried over sodium sulfate, filtered and concentrated. The residue was purified bycolumn chromatography on silica gel to yield benzyl {1-[methoxy(methyl)carbamoyl]cyclobutyl}carbamate as slightly yellow solid. MS ESI calc'd. forC1sHziNz04 [M + H]+ 293.1, found 293.3.

References:

WO2014/99836,2014,A1 Location in patent:Page/Page column 27