(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine → 7-[3-(R)-Aminopyrrolidinyl]-6,8-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 1939272Notes

Reaction equation

HRID 1939272 reaction equation
[F:1][C:2]1[C:3]([CH3:22])=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([C@@H:14]1[CH2:16][C@@H:15]1[F:17])[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21].C(OC([NH:30][C@@H:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)=O)(C)(C)C>>[NH2:30][C@@H:31]1[CH2:35][CH2:34][N:33]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:21])[C:6]([C:18]([OH:20])=[O:19])=[CH:7][N:8]3[C@@H:14]3[CH2:16][C@@H:15]3[F:17])=[C:3]([CH3:22])[C:2]=2[F:1])[CH2:32]1

Participants

3

Reactant 2

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 228799641-[(1R,2S)-2-Fluorocyclopropyl]-6,7,8-trifluoro-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

Product 1

HCID 228799687-[3-(R)-Aminopyrrolidinyl]-6,8-difluoro-1-[(1R,2S)-2-fluorocyclopropyl]-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidYield 66.1%

Procedure

A hundred milligrams of 6,7,8-trifluoro-1-[(1R,2S)-2-fluorocyclopropyl]-5-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and 120 mg of (R)-3-t-butoxycarbonylaminopyrrolidine were reacted in the same manner as in Example 7, and the reaction mixture was worked up similarly to yield 80 mg of the titled compound as a grayish white to yellowish white substance.

Sources & evidence

ORD record
ord-02ffca2aebc24538ac8a10fc355c536f
Source dataset
uspto-grants-1997_12
Patent number
US05696132

Reaction notes

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