benzyl 1,2,5-oxadiazepane-5-carboxylate synthesis

Yield:952153-89-8 74%

Reaction Conditions:

Stage #1: 5-benzyl-2-(tert-butyl) 1,2,5-oxadiazepane-2,5-dicarboxylatewith trifluoroacetic acid in chloroform at 20; for 19 h;
Stage #2: with sodium hydrogencarbonate in chloroform;water;

Steps:

973

Example 973 Synthesis of Compound 103 [Show Image] Compound 102 To a solution of BOC compound (101, 1.01g) in chloroform (25ml), trifluoroacetic acid (2ml) was added and stirred at room temperature for 19 hours. After the reaction, saturated aqueous NaHCO₃ was added, and the mixture was extracted with chloroform-methanol (9: 1). After dryness (Na₂SO₄), solvent was removed. The residue was purified by silica gel chromatography (hexane-ethyl acetate (1: 1)) to afford 526 mg (74 %) of Compound (102) as colorless syrup. 102: colorless syrup; 1H-NMR (300MHz, CDCl₃) δ 3.09 (t, 5.5, 1H), 3.14 (t, 5.5, 1H), 3.54-3.70 (m, 4H), 3.82 (t, 5.5, 1H), 3.91 (t, 5.5, 1H), 5.16 (s, 2H), 5.84 (br, NH), 7.29-7.40 (m, 5H)

References:

EP2009012,2008,A1 Location in patent:Page/Page column 329