D-2-FURYLALANINE

Off-white solid

According to certain embodiments: Y4 is ... D-phenyl-glycine, L-phenyl-glycine, D-H-4-hydroxy-phenyl-glycine, L-H-4-hydroxy-phenyl-glycine, In a 400 ml_ beaker, D-2-furyl alanine (8.16 g, 52.6 mmol; Chem-lmpex International, Inc., Wood Dale, IL) was slurried in water (200 ml_) with 10% Pd/C (0.85 g). The beaker was placed in the bottom of a 2L stainless steel autoclave, charged to 20 bar (290 psi) with hydrogen and stirred for 5 hours at RT. TLC (1 :1 :1 :1 :1 toluene/ acetone/butan-1 -ol/ water/acetic acid) showed some starting material remained. The reaction was re-charged with hydrogen to 20 bar and stirred overnight at RT, after which time TLC showed that starting material was no longer present. The mixture was filtered through a pad of celite (pad washed with 2 x 200ml water), and the combined filtrates stripped to afford (1-12a) as a brown solid that was a mixture of diastereomers (8.4 g, 52.8 mmol, 100%): 1 H NMR (400 MHz, TFA-d): delta 4.60 (2 H), 4.12 (2 H), 2.58 (1 H), 2.40 (2 H), 2.1 - 2.35 (4 H), 1 .89 (2 H).Example-91 4-((R)-1-Furan-2-ylmethyl-2-hydroxy-ethylamino)-2-trifluoromethyl-benzonitrile (R)-2-Amino-3-furan-2-yl-propionic acid (40 mg, 0.25 mmol) was reduced using the same procedure as described in Example-90. The crude was coupled with 4-Fluoro-2- trifluoromethyl-benzonitrile (19 mg, 0.1 mmol) and DIPEA (0.05 ml, 0.2 mmol) as in and gave 4-((R)-1-furan-2-ylmethyl-2-hydroxy-ethylamino)-2- trifluoromethyl-benzonitrile 11 mg (29%), after purification on HPLC, as a white solid.

Molecular Weight:155.15
XLogP3:-2.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:155.058243149
Monoisotopic Mass:155.058243149
Topological Polar Surface Area:76.5
Heavy Atom Count:11
Complexity:149
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes