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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 232046Generated: October 30, 2026

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

https://huagongshe.com/reaction/232046

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 535415—
Reactant(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 1514396—
SolventAcetonitrileHCID 6342—
Product(S)-1-Cyclopropyl-7-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl esterHCID 1455548299.5%

Reaction Steps

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°.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04851418
Source datasetuspto-grants-1989_07
ORD IDord-0b1dc134a20a45998a0a8b08855c0669
Source noteuspto-grants-1989_07