Phenylacetyl chloride → HCID 12917426, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (1126) (801 mg, 3.51 mmol) was dissolved in dry dichloromethane (DCM) (20 mL), cooled to ˜0° C. in an ice bath before adding triethylamine (0.587 mL, 4.21 mmol) followed by phenylacetyl chloride (0.514 mL, 3.86 mmol) in Dichloromethane (DCM) (5 mL) slowly over 5-10 mins. The reaction was then allowed to warm up to RT and stirred for 4 hours then left to stand overnight. LCMS run, desired material seen. Diluted with DCM (40 ml), washed with saturated sodium bicarbonate solution (45 ml). Aqueous layer extracted with DCM (2×30 ml). Combined extracts were washed with brine (45 ml), dried over Na2SO4, filtered and evaporated to afford a red gum of crude material. Purified on a SNAP 100 cartridge, eluting with DCM (3CV) to 100% 10% MeOH in DCM (12CV). Compound identified and solvent removed to afford an orange gum of desired product in 972 mg.

Provenance & Evidence