Triethylamine → (S)-1-Cyclopropyl-7-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester

HRID 232046Notes

Reaction equation

HRID 232046 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:23][C:24]([CH3:35])([O:26][C:27]([NH:29][C@H:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)=[O:28])[CH3:25].C(N(CC)CC)C>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:32]4[CH2:33][CH2:34][C@H:30]([NH:29][C:27]([O:26][C:24]([CH3:35])([CH3:25])[CH3:23])=[O:28])[CH2:31]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 14555482(S)-1-Cyclopropyl-7-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl esterYield 99.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 12.5 g (40 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester, 8.9 g (48 mmol) of (S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]pyrrolidine, 8.1 g (80 mmol) of triethylamine and 75 ml of acetonitrile was heated at reflux for 18 hours. The reaction mixture was cooled to 5° and the solid was removed by filtration, washed with acetonitrile, ether and dried in vacuo to give 19.0 g of the title compounds, mp 148°-151°.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture was cooled to 5°
  3. customthe solid was removed by filtration
  4. washwashed with acetonitrile, ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0b1dc134a20a45998a0a8b08855c0669
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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