6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylicacid

To a 4° C. solution of Part A compound (3.08 g, 22.5 mmol) in denatured ethanol (70 mL) was added a solution of glyoxylic acid monohydrate (2.0 g, 22 mmol) in ethanol (10 mL) dropwise. Shortly after the addition of glyoxylic acid, a white precipitate formed. The cooling bath was removed, and the reaction mixture was stirred for 2 h at ambient temperature. Filtration gave the title product (3.1 g, 73percent) as a white solid: LC/MS (electrospray, +ions) m/z 194(M+H).Triethylamine (0.76 mL, 0.55 g, 5.47 mmol) was added to a stirred solution of 3-(2-aminoethyl)phenol hydrochloride (1:1) 25a (1.00 g, 5.76 mmol) in EtOH (26 mL). The mixture was cooled to 5 °C and a solution of glyoxylic acid (0.53 g, 5.76 mmol) in EtOH (6 mL) was added drop wise. The resulting mixture was stirred for 1 hour with gradual warming to room temperature. The resulting solid was filtered and washed with EtOH to provide the title compound (0.78 g, 70percent yield) as an off-white solid. (ES+) m/z (M+1) 193.9.

Molecular Weight:193.20
XLogP3:-1.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:193.07389321
Monoisotopic Mass:193.07389321
Topological Polar Surface Area:69.6
Heavy Atom Count:14
Complexity:231
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes