BOC-BETA-IODO-ALA-OME

A mixture of triphenylphosphine (131 g, 0.500 mol) and imidazole (34 g, 0.50 mol) in DCM (600 mL) was cooled to 0 °C and iodide (127 g, 0.50 mol) was added in small portions over 0.5 h. The cooling bath was removed and the mixture was stirred for 0.5 h. After the mixture was re-cooled to 0 °C, a solution of (5)-methyl 2-((tert- butoxycarbonyl)amino)-3-hydroxypropanoate (73 g, 0.33 mol) in DCM (300 mL) was added dropwise. After the addition, the cooling bath was removed and the mixture was allowed to warm to ambient temperature and stirred for 1.5 h. The mixture was filtered and the filtrate was concentrated to remove most of the solvent. MTBE (400 mL) was added to the residue and the mixture was filtered to remove triphenylphosphine oxide. The filtrate was concentrated and the residue was purified by flash column chromatography on silica gel to afford (i?)-methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate (74.0 g, 68percent yield) as a colorless solid.Triphenylphosphite methiodide (Fieser and Fieser, Reagents for Organic Synthesis, Vol. 4, p557; 34Og, 753 mmol, 1.4 equiv.) was added in one portion to a solution of (S)-2- rert-butyloxycarbonylamino-3-hydroxypropionic acid methyl ester (118g, 538 mmol) in dry N, N-dimethylformamide (1.1 L) at 0°C. After 30 minutes at OTriphenylphosphine (66.0 g, 0.250 mol) and imidazole (17.1 g, 0.250 mol) were dissolved in methylene chloride (900 ml). After cooling to 0° C., iodine (64.0 g, 0.250 mol) was added thereto, and the temperature was gradually raised from 0° C. to room temperature in the presence of nitrogen gas, followed by stirring for 10 minutes. After cooling to 0° C., a methylene chloride solution (100 of methyl N-(tert-butoxycarbonyl)-L-serinate (45.0 g, 0.200 mol) was slowly added dropwise over one hour, followed by stirring at room temperature for 2 hours. After the reaction solution was filtered, the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1:1 to 1:2) to obtain the title compound (43.8 g, 65percent). [0585] 1H NMR (CDCl3, 400 MHz): δ 5.36-5.34 (m, 1H), 4.53-4.51 (m, 1H), 3.80 (s, 3H), 3.61-3.53 (m, 2H), 1.46 (s, 9H)

Molecular Weight:329.13
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:329.01241
Monoisotopic Mass:329.01241
Topological Polar Surface Area:64.6
Heavy Atom Count:15
Complexity:237
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes