BOC-7-AMINO-HEPTANOIC ACID

-iert-Butoxy-7-propiolamidoheptanamide (3- 1); 7-Aminohepatonic acid (726 mg, 5 mmol) was dissolved in a mixture solvent of ¾0 (3 mL)/dioxane (3 mL). To this solution, Et3N (2.08 mL, 15 mmol) was added followed by di- iert-butyl dicarbonate (1.72 mL, 7.5 mmol). The reaction mixture was kept room temperature and stirred for 7 nr. The After removed the organic solvent in vacuo, the solution was acidified by adding HC1 solution (3N) to pH~1.0 and extracted with EtOAc. The organic layer was collected and evaporated to give syrup which was treated with NaOH (IN) to pH~l 1.0 and washed with EtOAc. The aqueous phase was acidified to pH-1.0 and extracted with EtOAc. The organic layer was dried and evaporated to give syrup and was directly used for the next step. The above syrup was dissolved in (¾(¾ (50 mL) and treated with O- tButylhydroxylamine hydrochloride (1.00 g, 8.0 mmol), EDCI (1.59 g, 8.3 mmol), TEA (1.14 mL, 8.2 mmol), DMAP (183 mg, 1.5 mmol). After stirred at room temperature for 1.5 hr, the reaction mixture was washed with HC1 (IN) and the organic layer was collected and dried and evaporated to give syrup (1.57 g). The pale yellow syrup (1.30 g) was dissolved in TFA (10 mL) and stirred for 30 min. The excess TFA was completely removed in vacuo and the syrup was dissolved in CH2CI2 (50 mL) and treated with 3-(Trimethylsilyl)propynoic acid (701 mg, 5.0 mmol), EDCI (945 mg, 4.9 mmol), TEA (2.27 niL, 16.4 mmol), DMAP (100 mg, 0.82 mmol). After stirred at 50 C for 18 hr, the reaction mixture was washed with HC1 (IN) and dried over Na2SC<4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on a silica gel (EtOAc:Hexanes = 1: 1 - 1:2) to give a foam as compound 3-1 (600 mg, 4-step yield 42 ). NMR (300 MHz, CDClj) delta 3.25 (dt, J = 6.9 and 17.6 Hz, 2H), 2.12 (br, 2H), 1.64 (br, 2H), 1.51 (br, 2H), 1.33 (br, 4H), 1.25 (s, 9H), 0.21 (s, 9H).General procedure: A mixture of 33a-f (0.85 mmol), lenalidomide (0.77 mmol), pyridine(2.31 mmol) and phosphorus oxychloride (0.93 mmol) in acetonitrile(10 mL) was stirred at room temperature for 3 h. After the reactionwas completed, the mixture was concentrated and then dilutedwith water (10 mL) and extracted with ethyl acetate (10 mL × 3). Thecombined organic layer was dried over anhydrous Na2SO4 and concentratedunder reduced pressure. The crude residue was purified byflash column chromatography (dichloromethane/methanol = 35:1) to give 34a-f (about 40% yield).To a solution of

Molecular Weight:245.32
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:9
Exact Mass:245.16270821
Monoisotopic Mass:245.16270821
Topological Polar Surface Area:75.6
Heavy Atom Count:17
Complexity:245
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes