Hydrochloric Acid → HCID 68907622, compound

HRID 1510348Notes

Reaction equation

HRID 1510348 reaction equation
C(OC([NH:8][C:9]1([CH3:37])[C:13]2([CH2:15][CH2:14]2)[CH2:12][N:11]([C:16]2[C:25]([O:26][CH3:27])=[C:24]3[C:19]([C:20](=[O:35])[C:21]([C:32]([OH:34])=[O:33])=[CH:22][N:23]3[C@@H:28]3[CH2:30][C@@H:29]3[F:31])=[CH:18][C:17]=2[F:36])[CH2:10]1)=O)(C)(C)C.[ClH:38]>C(O)(C)C>[ClH:38].[NH2:8][C:9]1([CH3:37])[C:13]2([CH2:14][CH2:15]2)[CH2:12][N:11]([C:16]2[C:25]([O:26][CH3:27])=[C:24]3[C:19]([C:20](=[O:35])[C:21]([C:32]([OH:34])=[O:33])=[CH:22][N:23]3[C@@H:28]3[CH2:30][C@@H:29]3[F:31])=[CH:18][C:17]=2[F:36])[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57758693HCID 57758693, compound

Product 1

HCID 68907622HCID 68907622, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
55 °C

Procedure

7-[7-(tert-Butoxycarbonylamino)-7-methyl-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid in which configuration of the tert -butoxycarbonylamino group in the substituent at position 7 is the same as the one produced in Example 9 (267.2 g) was suspended in isopropyl alcohol (1.6 L), and 6N hydrochloric acid (405 mL, 2.43 mol) was added to the suspension while the suspension was stirred in an oil bath at 55° C. The mixture was stirred at the same temperature for 3.5 hours, and after allowing to cool to room temperature, isopropyl alcohol (2.4 L) was added. The reaction vessel was cooled in a water bath at 5° C., and the mixture was stirred at the same temperature for 13 hours. The precipitated crystals were collected by filtration and after air drying for several hours, the crystals were dried under reduced pressure at 40° C. to obtain 223.3 g (471 mmol, 92%) of the target compound as a yellow powder.

Workup

  1. stirringThe mixture was stirred at the same temperature for 3.5 hours
  2. temperatureto cool to room temperature
  3. temperatureThe reaction vessel was cooled in a water bath at 5° C.
  4. stirringthe mixture was stirred at the same temperature for 13 hours
  5. filtrationThe precipitated crystals were collected by filtration
  6. customafter air drying for several hours
  7. customthe crystals were dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-d89671350f0b4e24a6d02f785272ff43
Source dataset
uspto-grants-2012_07
Patent number
US08211910B2

Reaction notes

Loading…