Water → HCID 13631270, compound

Participants

Reaction Steps

(S)-1-[[[(4-Methylphenyl)sulfonyl]amino]-carbonyl]-2oxo-3-aminoazetidine, triethylammonium salt (626 mg, see example 2) was dissolved in dry acetonitrile (25 ml) and stirred under nitrogen in an ice bath. Triethylamine (0.57 ml) was added, followed by phenylacetyl chloride (0.324 ml). After 3 hours an equal volume of water was added, the pH was adjusted to 7.5, and the acetonitrile was removed in vacuo. The aqueous residue was extracted twice with ethyl acetate to remove neutral material. The aqueous layer was then acidified to pH 2.0 and extracted three times with ethyl acetate. The acidic extract was dried over anhydrous sodium sulfate and evaporated to dryness in vacuo, yielding 544 mg. This crude product, and an additional 481 mg of crude product from two other runs were combined and purified by chromatography on a column of SilicAR CC-4 (100 g), using dichloromethane and dichloromethane:methanol, 99:1 as eluants. The amorphous product was crystallized from acetonitrile to give 154 mg of crystalline material, melting point 170°-172° C.

Provenance & Evidence