Hydrochloric Acid → (+/-)-(E)-3-{1'-methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-N-hydroxy-acrylamide

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	(+/-)-(E)-3-{1'-methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide	HCID 86671993	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(+/-)-(E)-3-{1'-methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-N-hydroxy-acrylamide	HCID 51357827	64.2%

Reaction Steps

A solution of (±)-(E)-3-{1′-methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3′-piperidin]-6-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide (210 mg, 0.52 mmol) in DCM (6 ml) was treated with 4 M HCl in dioxane (1.0 ml) as described in Example 30, STEP C to give (±)-(E)-3-{1′-methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3′-piperidin]-6-yl}-N-hydroxy-acrylamide (106 mg, hydrochloride salt) as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08980877B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-bd8c52616e7a41c6927aad5bb8ca55af
Source note	uspto-grants-2015_03