Boc-D-Homoserine lactone → HCID 66972798, compound

Participants

Reaction Conditions

Reaction Steps

Clean sodium metal (0.205 g, 8.95 mmol) was added, in portions, to anhydrous methanol (20 mL) in a thick walled tube. The suspension was stirred under anhydrous nitrogen until all the metal had dissolved, then pyridine-2-thiol (1.0 g, 8.95 mmol) was added. After stirring for 20 min, (2-oxotetrahydro-furan-3(R)-yl)-carbamic acid tert-butyl ester (1.8 g, 8.95 mmol) was added as a solid and the tube was capped and heated to 100° C. for 16 h. The reaction mixture was concentrated, then purified via flash chromatography (MeOH, CH2Cl2 as eluent) to give 2(S)-tert-butoxycarbonylamino-4-(pyridin-2-ylsulfanyl)butyric acid (0.75 g) as a clear oil.

Provenance & Evidence