Trifluoroacetic acid → HCID 86744592, compound

HRID 981284Notes

Reaction equation

FC(F)(F)C(O)=O.C([O:12][C:13]([CH:15]1[CH2:17][CH:16]1[C:18]1[C:19]([F:38])=[CH:20][C:21]2[C:31](=[O:32])[C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][N:23]3[C@@H:24]([CH3:28])[CH2:25][O:26][C:27]=1[C:22]=23)=[O:14])(C)(C)C>>[C:13]([CH:15]1[CH2:17][CH:16]1[C:18]1[C:19]([F:38])=[CH:20][C:21]2[C:31](=[O:32])[C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][N:23]3[C@@H:24]([CH3:28])[CH2:25][O:26][C:27]=1[C:22]=23)([OH:14])=[O:12]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86744593HCID 86744593, compound

Product 1

HCID 86744592HCID 86744592, compoundYield 92.9%

Procedure

5 ml of trifluoroacetic acid was added to 570 mg of ethyl (S)-10-(2-tert-butoxycarbonylcyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate. The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. Diethyl ether was added to the residue obtained. The resulting crystals were collected by filtration to obtain 460 mg (yield: 92.9%) of ethyl (S)-10-(2-carboxycyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionDiethyl ether was added to the residue
customobtained
filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record: ord-4a0e8641ebe24109bd92c6672980afaf
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04990508

Reaction notes

Loading…