Hydroxyamine hydrochloride → (2'R,4'S,4'aS)-9',10'-difluoro-8'-[(E)-N-hydroxy-C-phenylcarbonimidoyl]-2',4'-dimethylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1H-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione

HRID 577822Notes

Reaction equation

Cl.[NH2:2][OH:3].[F:4][C:5]1[C:22]([F:23])=[C:21]2[C:8]([CH2:9][C:10]3([C@H:19]4[C@H:27]([CH3:28])[O:26][C@H:25]([CH3:29])[CH2:24][N:20]42)[C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12][C:11]3=[O:18])=[CH:7][C:6]=1[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=O>CO.N1C=CC=CC=1>[F:4][C:5]1[C:22]([F:23])=[C:21]2[C:8]([CH2:9][C:10]3([C@H:19]4[C@H:27]([CH3:28])[O:26][C@H:25]([CH3:29])[CH2:24][N:20]42)[C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12][C:11]3=[O:18])=[CH:7][C:6]=1/[C:30](=[N:2]/[OH:3])/[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Hydroxylamine hydrochloride (77 mg, 0.001 mmol) was added to a solution of (2R,4S,4aS)-rel-9,10-difluoro-2,4-dimethyl-8-(phenylcarbonyl)-1,2,4,4a-tetrahydro-2′H,6H-spiro[1,4-oxazino[4,3-a]quinoline-5,5′-pyrimidine]-2′,4′,6′(1′H,3′H)-trione (Intermediate 13, 280 mg, 0.6 mmol) in methanol:pyridine (1:1, 3 mL) and the solution was heated to 90° C. for 12 hours. Solvents were removed and the residue was subjected to silica gel column chromatography using a gradient of ethyl acetate in pet. ether to give the title compound as a racemic mixture. Yield: 120 mg (42%).

Workup

customSolvents were removed

Sources & evidence

ORD record: ord-0b80ef25e657465abc1aa9b3b681edb2
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040528B2

Reaction notes

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