Water → Ciprofloxacin (S)-5-Oxotetrahydrofuran-2-carboxylate

HRID 375082

Reaction equation

HRID 375082 reaction equation
[O:1]=[C:2]1[O:6][C@H:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3]1.[CH:10]1[C:11]2[C:26](=[O:27])[C:25]([C:28]([OH:30])=[O:29])=[CH:24][N:23]([CH:31]3[CH2:33][CH2:32]3)[C:12]=2[CH:13]=[C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:15]=1[F:16].O>CC(C)=O>[CH:10]1[C:11]2[C:26](=[O:27])[C:25]([C:28]([OH:30])=[O:29])=[CH:24][N:23]([CH:31]3[CH2:32][CH2:33]3)[C:12]=2[CH:13]=[C:14]([N:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)[C:15]=1[F:16].[O:1]=[C:2]1[O:6][C@H:5]([C:7]([O-:9])=[O:8])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 2764CiprofloxacinHCID 636468(2S)-5-oxooxolane-2-carboxylic acid

Product 1

HCID 86749207Ciprofloxacin (S)-5-Oxotetrahydrofuran-2-carboxylateYield 82.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.781 G (0.006 mole) of (S)-5-oxotetrahydrofuran-2-carboxylic acid and 1.99 g (0.006 mole) of Ciprofloxacin were added to 10 mL of distilled water. The resulting mixture was stirred for 30 minutes to dissolve it completely. After adding 20 mL of anhydrous acetone, the resulting solution was further stirred for 30 minutes under ice-cooling and allowed to stand to precipitate solids. The precipitated solids were filtered under reduced pressure through a filter paper (Whatman Filter Paper No. 1), washed three times with each 30 mL of anhydrous acetone,-and dried under vacuum to give 2.27 g of the titled compound as white solids. M.P. 214°-219° C. (decomposition) [α]D25 =-3.33 (H2O)

Workup

  1. dissolutionto dissolve it completely
  2. stirringthe resulting solution was further stirred for 30 minutes under ice-
  3. temperaturecooling
  4. customto precipitate solids
  5. filtrationThe precipitated solids were filtered under reduced pressure through a filter paper (Whatman Filter Paper No. 1)
  6. washwashed three times with each 30 mL of anhydrous acetone
  7. customdried under vacuum

Sources & evidence

ORD record
ord-7bd91dfc2ada4f2aa7ccd5f589a1797c
Source dataset
uspto-grants-1996_01
Patent number
US05484785

Linked notes

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