Hydroxyamine hydrochloride → HCID 9887810, compound

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Reaction Steps

A solution of 5-chloro-1H-indole-2-carboxylic acid [(1S)-benzyl-2-(3-oxo-azetidin-1-yl)-2-oxo-ethyl]-amide (product of Example 170, 50 mg, 0.13 mmol), sodium acetate trihydrate (43 mg, 0.32 mmol) and hydroxylamine hydrochloride (18 mg, 0.25 mmol) in methanol (2 mL) was heated at reflux for 8 h and concentrated. The residue was partitioned between dichloromethane and saturated aqueous NaHCO3. The organic layer was separated and dried giving a colorless solid which was triturated with ether-hexanes and dried (yield 36 mg, 69%): HPLC (50/50) 6.74 min (99%); TSPMS 411/413 (MH+, 10%), 180 (100%); 1H NMR (DMSO-d6) δ 11.75 (br, 1H), 11.10 (s, 0.5H), 11.08 (s, 0.5H), 8.99 (d, 1H, J=9 Hz), 7.73 (d, 1H, J=2 Hz), 7.4-7.1 (m, 8H), 5.0 (m, 1H), 4.84.5 (m, 4H), 3.1 (m, 2H).

Provenance & Evidence