Hydroxylamine → (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

Participants

Role	Name	HCID	Charge
Reactant	Hydroxylamine	HCID 787	—
Reactant	Erythromycin	HCID 12560	—
Product	(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one	HCID 6537896	—

reacting the C-9 ketone of erythromycin A with hydroxylamine to form erythromycin oxime;