(S)-tert-Butyl 5-azaspiro[2.4]heptan-7-ylcarbamate → 5-acetylamino-7-[(7S)-7-tert-butoxycarbonylamino-5-azaspiro[2.4]hept-5-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid

HRID 2417233Notes

Reaction equation

[C:1]([NH:4][C:5]1[C:14]([F:15])=[C:13](F)[C:12]([CH3:17])=[C:11]2[C:6]=1[C:7](=[O:24])[C:8]([C:21]([OH:23])=[O:22])=[CH:9][N:10]2[CH:18]1[CH2:20][CH2:19]1)(=[O:3])[CH3:2].[C:25]([O:29][C:30]([NH:32][C@H:33]1[C:37]2([CH2:39][CH2:38]2)[CH2:36][NH:35][CH2:34]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>CS(C)=O>[C:1]([NH:4][C:5]1[C:14]([F:15])=[C:13]([N:35]2[CH2:34][C@@H:33]([NH:32][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[C:37]3([CH2:38][CH2:39]3)[CH2:36]2)[C:12]([CH3:17])=[C:11]2[C:6]=1[C:7](=[O:24])[C:8]([C:21]([OH:23])=[O:22])=[CH:9][N:10]2[CH:18]1[CH2:20][CH2:19]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture consisting of 5-acetylamino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid (51.2 mg), (7S)-7-tert-butoxycarbonylamino-5-azaspiro(2.4)heptane (48.2 mg) and dimethyl sulfoxide (0.25 ml) was stirred at an outer temperature of 95° C. for 20 hours. When quantitative analysis was carried out by a high performance liquid chromatography after completion of the reaction, formed amount of the compound of interest 5-acetylamino-7-[(7S)-7-tert-butoxycarbonylamino-5-azaspiro[2.4]hept-5-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid corresponded to 68.9 mg. The formation ratio was 85.6%.

Workup

customafter completion of the reaction

Sources & evidence

ORD record: ord-a3b19193c2344b9796dd76d69416721c
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825353B2

Reaction notes

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