(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 1078275Notes

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: 100 °C

Procedure

A mixture of 20.0 g of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid, 28.9 g of (S)-7-tert-butoxycarbonylamino-5-azaspiro[2.4]heptane ([α]D20 -47.2° (c=1, MeOH)) and 80 ml of dimethyl sulfoxide was heated at 100° C. for 36 hours. The reaction mixture was poured into 500 ml of ice water. The deposited crystals were collected by filtration, washed with water and isopropanol, and then recrystallized from a mixture of methylene chloride and methanol to give 14.7 g of the desired compound, which was identified as the compound of Example 19.

Workup

filtrationThe deposited crystals were collected by filtration
washwashed with water and isopropanol
customrecrystallized from a mixture of methylene chloride and methanol

Sources & evidence

ORD record: ord-ccdad7b3f957448ab7c27542f2c84157
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05547962

Reaction notes

Loading…