Ciprofloxacin → 1-Cyclopropyl-7-[4-(diethoxyphosphinyl)-1-piperazinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

HRID 1460150

Reaction equation

HRID 1460150 reaction equation
[CH:1]1[C:2]2[C:17](=[O:18])[C:16]([C:19]([OH:21])=[O:20])=[CH:15][N:14]([CH:22]3[CH2:24][CH2:23]3)[C:3]=2[CH:4]=[C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:6]=1[F:7].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[P:37](Cl)([O:42][CH2:43][CH3:44])([O:39][CH2:40][CH3:41])=[O:38]>C(Cl)Cl>[CH:22]1([N:14]2[C:3]3[C:2](=[CH:1][C:6]([F:7])=[C:5]([N:8]4[CH2:9][CH2:10][N:11]([P:37]([O:42][CH2:43][CH3:44])([O:39][CH2:40][CH3:41])=[O:38])[CH2:12][CH2:13]4)[CH:4]=3)[C:17](=[O:18])[C:16]([C:19]([OH:21])=[O:20])=[CH:15]2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 2764CiprofloxacinHCID 13139Diethyl chlorophosphateHCID 6913588N,O-bis(trimethylsilyl)acetamide

Product 1

HCID 150280071-Cyclopropyl-7-[4-(diethoxyphosphinyl)-1-piperazinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 2.816 g (8.5 mmol) of ciprofloxacin base in 100 ml of dry CH2Cl2 was stirred under argon as 3.46 g (17 mmol) of N,O-bis(trimethylsilyl)acetamide was added. After the solid had dissolved (2-3 hours), 1.47 g (8.5 mmol) of diethyl chlorophosphate was added. After 24 hours at approximately 23° the solution was evaporated, finally at 0.03 mm for 15 hours. Washing of the solid residue with water gave a white solid which was dried and then recrystallized from CH2Cl2 -toluene, boiling out the CH2Cl2 within 10 minutes to avoid thermal degradation. The product was 3.74 g (94%) of cream-colored solid, m.p. 192°-193° C.; NMR (CDCl3, 80 MHz) δ 1.36 (t, CH3), 3.30 (s, CH2N), 4.06 (5 peaks, OCH2); IR (KBr) 1028(P=O), 1630 (--COOH), 1724 cm-1 (C=O).

Workup

  1. additionwas added
  2. additionwas added
  3. customAfter 24 hours at approximately 23° the solution was evaporated, finally at 0.03 mm for 15 hours
  4. washWashing of the solid residue with water
  5. customgave a white solid which
  6. customwas dried
  7. customrecrystallized from CH2Cl2 -toluene

Sources & evidence

ORD record
ord-090f9408ecdb44d3a5c2110dce2481bb
Source dataset
uspto-grants-1991_12
Patent number
US05070082

Linked notes

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