7-(3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid → 7-(3-Amino-4-methyl-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580573Notes

Reaction equation

HRID 580573 reaction equation
C(OC([NH:8][CH:9]1[CH:13]([CH3:14])[CH2:12][N:11]([C:15]2[C:24]([Cl:25])=[C:23]3[C:18]([C:19](=[O:32])[C:20]([C:29]([OH:31])=[O:30])=[CH:21][N:22]3[CH:26]3[CH2:28][CH2:27]3)=[CH:17][C:16]=2[F:33])[CH2:10]1)=O)(C)(C)C>CO.Cl>[NH2:8][CH:9]1[CH:13]([CH3:14])[CH2:12][N:11]([C:15]2[C:24]([Cl:25])=[C:23]3[C:18]([C:19](=[O:32])[C:20]([C:29]([OH:31])=[O:30])=[CH:21][N:22]3[CH:26]3[CH2:28][CH2:27]3)=[CH:17][C:16]=2[F:33])[CH2:10]1

Participants

4

Reactant 1

HCID 139330937-(3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 139330957-(3-Amino-4-methyl-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 25.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

7-(3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.35 g) was dissolved in the mixture of methanol (5 ml) and concentrated hydrochloric acid (5 ml) and stirred at room temperature for 30 minutes. After the reacting mixture was concentrated under reduced pressure, the resulting residue was dissolved in ethanol (10 ml) and neutralized with concentrated aqueous ammonia. The resulting precipitate was collected by filtration, washed with water and recrystallized from chloroformmethanol-concentrated aqueous ammonia to give the title compound (0.07 g) as pale yellow powder, mp 231°-234° C.

Workup

  1. concentrationAfter the reacting mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in ethanol (10 ml) and neutralized with concentrated aqueous ammonia
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customrecrystallized from chloroformmethanol-concentrated aqueous ammonia

Sources & evidence

ORD record
ord-77fdf73eb585441895742b6ccae3bd55
Source dataset
uspto-grants-1988_06
Patent number
US04753953

Reaction notes

Loading…