1,2-Dichloroethane → HCID 67128600, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [3-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-acetic acid (2.20 g, 9.90 mmol) in CH2Cl2 (100 mL) was treated sequentially with DMAP (301 mg, 2.47 mmol), HOBT (1.61 g, 11.90 mmol), EDC (4.74 g, 24.75 mmol) and DIPEA (6.78 mL, 39.60 mmol). After stirring for 30 min at rt, serine methylester hydrochloride (1.62 g, 10.39 mmol) was added and the reaction mixture stirred overnight at rt. Water (100 mL) was added and the mixture was extracted twice with CH2Cl2 (100 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (97:3 EA-MeOH) gave the title compound as a brown oil. TLC: rf (97:3 EA-MeOH)=0.45. LC-MS-conditions 02: tR=0.74 min; [M+H]+=324.41.

Provenance & Evidence