(S)-tert-Butyl 5-azaspiro[2.4]heptan-7-ylcarbamate → 5-amino-7-((S)-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 2417242Notes

Reaction equation

[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([CH3:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[C:22]([O:26][C:27]([NH:29][C@H:30]1[C:34]2([CH2:36][CH2:35]2)[CH2:33][NH:32][CH2:31]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:32]2[CH2:31][C@@H:30]([NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[C:34]3([CH2:35][CH2:36]3)[CH2:33]2)[C:9]([CH3:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture consisting of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid (50 mg, 0.170 mmol), (7S)-7-tert-butoxycarbonylamino-5-azaspiro[2.4]heptane (108 mg, 0.509 mmol) and dimethyl sulfoxide (4 ml) was stirred at an outer temperature of 80° C. for 7 hours. When analysis was carried out by a high performance liquid chromatography after completion of the reaction, formed ratio of the compound of interest 5-amino-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 was 10%. Also, residual ratio of the starting material was 90%.

Workup

customafter completion of the reaction

Sources & evidence

ORD record: ord-012e93f2beeb458d86bc3b4b54b8757a
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825353B2

Reaction notes

Loading…