Chlorotrimethylsilane → 6-[[(1-Acetyl-2-pyrrolidinyl)-carbonyl]amino]-1,4-dihydro-4-oxo-quinolinecarboxylic acid

HRID 851003

Reaktionsgleichung

Reaktionsgleichung von HRID 851003
[C:1]([N:4]1[CH2:11][CH2:10][CH2:9][C@H:5]1[C:6]([OH:8])=O)(=[O:3])[CH3:2].Cl[C:13]([O:15]CC(C)C)=[O:14].CN1CCOCC1.[NH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][CH:33]=[C:32](C(O)=O)[C:31]2=[O:41].C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl>[C:1]([N:4]1[CH2:11][CH2:10][CH2:9][CH:5]1[C:6]([NH:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]([C:13]([OH:15])=[O:14])=[CH:32][C:31]2=[O:41])=[O:8])(=[O:3])[CH3:2]

Komponenten

8

Edukt 6

HCID 6397ChlorotrimethylsilaneHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 66141N-Acetyl-L-prolineHCID 32812016-Amino-4-hydroxyquinoline-3-carboxylic acid

Produkt 1

HCID 705242476-[[(1-Acetyl-2-pyrrolidinyl)-carbonyl]amino]-1,4-dihydro-4-oxo-quinolinecarboxylic acidAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 7.07 g (45 mmol) of N-acetyl-L-proline, 5.85 ml (45 mmol) isobutyl chloroformate, 4.95 ml 45 mmol) N-methyl morpholine, and 90 ml of dichloromethane is stirred at -10° to -20° for 30 minutes. A mixture of 6.13 g (30 mmol) of 6-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 12.6 ml (90 mmol) triethylamine, 11.4 ml (90 mmol) chlorotrimethylsilane, and 150 ml of dichloromethane is stirred at room temperature for 30 minutes and then is cooled to -20°. The cold mixed anhydride solution is added to the cold silylated quinoline and is stirred with cooling for 4 hours and at room temperature ovenight. The reaction mixture is evaporated to dryness and the residue is treated with 1 N hydrochloric acid and the solid is filtered. The solid is digested with ethanol and filtered to give 6.43 g of 6-[[(1-acetyl- 2-pyrrolidinyl)-carbonyl]amino]-1,4-dihydro-4-oxo-quinolinecarboxylic acid.

Aufarbeitung

  1. stirringis stirred at room temperature for 30 minutes
  2. temperatureis cooled to -20°
  3. stirringis stirred
  4. customThe reaction mixture is evaporated to dryness
  5. additionthe residue is treated with 1 N hydrochloric acid
  6. filtrationthe solid is filtered
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-23759aa6377740ca9a078275182f5948
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04382089

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