Potassium Hydroxide → HCID 67732729, compound

HRID 743646Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:5][N:4]([C:6]2[C:7]([F:29])=[CH:8][C:9]3[C:10]([CH:28]=2)=[N:11][C:12]2[N:13]([CH:25]4[CH2:27][CH2:26]4)[CH:14]=[C:15]([C:20]([O:22]CC)=[O:21])[C:16](=[O:19])[C:17]=2[CH:18]=3)[C@H:3]1[CH3:30].[OH-].[K+]>O>[NH2:1][C@@H:2]1[CH2:5][N:4]([C:6]2[C:7]([F:29])=[CH:8][C:9]3[C:10]([CH:28]=2)=[N:11][C:12]2[N:13]([CH:25]4[CH2:26][CH2:27]4)[CH:14]=[C:15]([C:20]([OH:22])=[O:21])[C:16](=[O:19])[C:17]=2[CH:18]=3)[C@H:3]1[CH3:30]

Participants

Conditions

Temperature: 95 °C

Procedure

A suspension of 1.4 g of 8-(trans-3-amino-2-methyl-1-azetidinyl)-1-cyclopropyl-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine in 15 cm3 of water and 6.8 cm3 of N aqueous potassium hydroxide is heated to approximately 95° C. for 3 hours. After cooling to approximately 60° C., some very slight insoluble matter is removed by filtration; at the same temperature, 6.8 cm3 of N methanesulphonic acid are added to the filtrate. The insoluble matter formed is drained at approximately 20° C. and washed with 3 times 50 cm3 of water and twice 25 cm3 of ethanol. After recrystallization in 30 cm3 of dimethylformamide, one obtains 1.03 g of 8-(trans-3-amino-2-methyl-1-azetidinyl)-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid in the form of a yellow solid, which decomposes at 268°-270° C.

Workup

temperatureAfter cooling to approximately 60° C.
customsome very slight insoluble matter is removed by filtration
additionat the same temperature, 6.8 cm3 of N methanesulphonic acid are added to the filtrate
customThe insoluble matter formed
customis drained at approximately 20° C.
washwashed with 3 times 50 cm3 of water and twice 25 cm3 of ethanol
customAfter recrystallization in 30 cm3 of dimethylformamide

Sources & evidence

ORD record: ord-c9d6177ba9bb45de9ad187fc8c93d624
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556861

Reaction notes

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