3-Cyano-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine

off-white to light yellow crystalline powder

Boc-3-cyano-(L)-phenylalanine Boc-3-cyano-(L)-phenylalanine To a cold (0 C) DCM (5ml) solution was added General procedure: General Procedure A: Gen eral procedure for the synthesis of amides (20):A solution of A dry, 75 mL heavy walled reaction tube was equipped with a stir bar and was charged with 3 (150 mg, 0.52 mmol), Ni(OTf)2 (91.3 mg, 0.26 mmol), and acetonitrile (0.27 mL, 5.2 mmol). The flask was purged with argon for 20 minutes. Anhydrous hydrazine was added to the mixture (0.82 mL, 26 mmol), the tube was sealed, and the reaction mixture was heated to 60C for 24 hr. The reaction was allowed to cool to room temperature and slowly opened to air. Sodium nitrite (2 M, 5.2 mL) was added to the flask. The reaction mixture was diluted with 50 mL water. Subsequently, the organic byproducts were exacted with EtOAc (3x), combined, and washed with water (2x) to regain any lost product. The aqueous layers were combined and the contents were cooled to 0C. 1 N HC1 was added slowly until gas evolution ceased and the pH of the mixture was acidic (about 3). The mixture was then diluted with EtOAc and the layers separated. The aqueous layer was extracted with EtOAc (2x). The combined organic layers were washed with brine, dried with Na2S04, and concentrated under reduced pressure. Silica gel flash column chromatography (50% ethyl acetate in hexanes with 1% acetic acid) yielded 113 mg of 4 (0.325 mmol, 61%) in the form of a red oil. R^0.33 in 50% ethyl acetate in hexanes with 1% acetic acid. 1H NMR (400 MHz, CDC13) delta 8.44 (t, 2H), 7.51 (m, 2H), 5.19 (d, 1H), 4.73 (d, 1H), 3.38-3.24 (dd, 2H), 3.11 (s, 3H), 1.42 (s, 9H).General procedure: (S)-2-((tert-Butoxycarbonyl)amino)-3-phenylpropanoic acid (compound 5a, 203.6 mg, 0.768 mmol) in DMF (5 mL) was added HOBt (283.2 mg, 2.10 mmol) and EDCI (257.8 mg, 1.396 mmol). After stirring for 30 min compound 4 (187.2 mg, 0.698 mmol) and additional TEA (0.30 mL, 2.10 mmol) were added. This solution was allowed to stir at room temperature for 20 h and then the saturated NaHCO3 was added. The mixture was extracted with EtOAc and washed with saturated NaCl, dried over Na2SO4 and concentrated. The residue was purified with flash chromatography on silica gel, eluted with a mixture of PE/EA (4/1, v/v) to afford 6a (130 mg, 54%) as a white solid.

Molecular Weight:290.31
XLogP3:2.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:290.12665706
Monoisotopic Mass:290.12665706
Topological Polar Surface Area:99.4
Heavy Atom Count:21
Complexity:433
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes