METHYL (2R)-2-AMINO-3-(THIOPHEN-2-YL)PROPANOATE synthesis

Yield:294887-34-6 69%

Reaction Conditions:

Stage #1: methanolwith acetyl chloride at 0; for 0.25 h;
Stage #2: D-2-amino-3-thiophen-2-yl-propionic acid
Stage #3: with sodium hydrogencarbonate in dichloromethane;water;

Steps:

119.1

AcCI (4.15 mL, 58.5 mmol) was added dropwise in MeOH (50 mL) at 0⁰C. The solution was stirred 15 min then (R)-2-amino-3-(thiophen-2-yl)propanoic acid (2.0 g, 11.7 mmol) was added and stirred over night. The solvent was concentrated and the residue was dissolved in DCM, washed with NaHCO_3(aq), dryed with sodium sulfate and concentrated under vacuum to afford the title compound 131c (1.5 g, 69%). LRMS (ESI): (calc.) 185.4; (found) 186.1 (MH) ⁺.

References:

WO2007/22638,2007,A1 Location in patent:Page/Page column 109; 111