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

HRID 874315Notes

Reaction equation

HRID 874315 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C:4]2([NH:12][C:11](=[O:13])[C:10]3[CH:14]=[C:15](/[CH:18]=[CH:19]/[C:20]([NH:22][O:23]C4CCCCO4)=[O:21])[CH:16]=[CH:17][C:9]=3[O:8]2)[CH2:3]1.Cl>C(Cl)Cl.O1CCOCC1>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C:4]2([NH:12][C:11](=[O:13])[C:10]3[CH:14]=[C:15](/[CH:18]=[CH:19]/[C:20]([NH:22][OH:23])=[O:21])[CH:16]=[CH:17][C:9]=3[O:8]2)[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86671993(+/-)-(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

Product 1

HCID 51357827(+/-)-(E)-3-{1'-methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-N-hydroxy-acrylamideYield 64.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Sources & evidence

ORD record
ord-bd8c52616e7a41c6927aad5bb8ca55af
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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