Acetic Acid → HCID 69620851, compound

Participants

Reaction Steps

L-Phenylalanine methyl ester HCl 34.8.A (2.15 g, 10.0 mmol) was partitioned with DCM and saturated NaHCO3. The aqueous layer was extracted with DCM (2×). The organic layers were combined, dried with sodium sulfate, filtered, and concentrated. The residue was dissolved in DCM (30 ml) and AcOH (571 μL, 10 mmol), thiazole-4-carboxaldehyde 34.8.B (1.13 g, 10 mmol), and NaBH(OAc)3 (4.24 g, 20 mmol) were added and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with NaHCO3(sat) and extracted with DCM. The organic extracts were dried with sodium sulfate, filtered, and concentrated. The resulting residue was partially purified on a silica gel column (120 g, 0-8% MeOH:DCM) to yield 34.8.0 as a crude oil (2.25 g).

Provenance & Evidence