Hydrochloric Acid → Olamufloxacin

HRID 2417234Notes

Reaction equation

HRID 2417234 reaction equation
[OH-].[Na+].C([NH:6][C:7]1[C:16]([F:17])=[C:15]([N:18]2[CH2:24][C@@H:23]([NH:25]C(OC(C)(C)C)=O)[C:20]3([CH2:22][CH2:21]3)[CH2:19]2)[C:14]([CH3:33])=[C:13]2[C:8]=1[C:9](=[O:40])[C:10]([C:37]([OH:39])=[O:38])=[CH:11][N:12]2[CH:34]1[CH2:36][CH2:35]1)(=O)C.Cl>>[NH2:6][C:7]1[C:16]([F:17])=[C:15]([N:18]2[CH2:24][C@@H:23]([NH2:25])[C:20]3([CH2:21][CH2:22]3)[CH2:19]2)[C:14]([CH3:33])=[C:13]2[C:8]=1[C:9](=[O:40])[C:10]([C:37]([OH:39])=[O:38])=[CH:11][N:12]2[CH:34]1[CH2:36][CH2:35]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 121332225-acetylamino-7-[(7S)-7-tert-butoxycarbonylamino-5-azaspiro[2.4]hept-5-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 477670Olamufloxacin

Procedure

A 20% sodium hydroxide aqueous solution (4.8 ml) was added to 76.7% purity 5-acetylamino-7-[(7S)-7-tert-butoxycarbonylamino-5-azaspiro[2.4]hept-5-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid (400.1 mg) under stirring at room temperature, and the mixture was stirred at 80° C. for 5 hours. While stirring at room temperature, the reaction solution was mixed with concentrated hydrochloric acid and stirred for 1 hour. When quantitative analysis was carried out by a high performance liquid chromatography after neutralization of the reaction solution by adding 20% sodium hydroxide aqueous solution, formed amount of the compound of interest 5-amino-7-[(7S)-7-amino-5-azaspiro[2.4]hept-5-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid corresponded to 207.2 mg. The formation ratio was 92%.

Workup

  1. stirringthe mixture was stirred at 80° C. for 5 hours
  2. stirringWhile stirring at room temperature
  3. stirringstirred for 1 hour

Sources & evidence

ORD record
ord-d48935f8c9d24594bdb5eef6e633245a
Source dataset
uspto-grants-2004_11
Patent number
US06825353B2

Reaction notes

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