Chlorotrimethylsilane → 7-[[2-(Acetylamino)-1-oxopropyl]-amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 851005

Reaction equation

HRID 851005 reaction equation
[C:1]([NH:4][C@H:5]([C:7]([OH:9])=O)[CH3:6])(=[O:3])[CH3:2].CN1CCOCC1.ClC(OC)=O.[NH2:22][C:23]1[CH:32]=[C:31]2[C:26]([C:27](=[O:36])[C:28]([C:33]([OH:35])=[O:34])=[CH:29][NH:30]2)=[CH:25][CH:24]=1.C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl.C(#N)C>[C:1]([NH:4][CH:5]([CH3:6])[C:7]([NH:22][C:23]1[CH:32]=[C:31]2[C:26]([C:27](=[O:36])[C:28]([C:33]([OH:35])=[O:34])=[CH:29][NH:30]2)=[CH:25][CH:24]=1)=[O:9])(=[O:3])[CH3:2]

Participants

9

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 88064N-Acetyl-L-alanineHCID 102623227-Amino-4-hydroxyquinoline-3-carboxylic acid

Product 1

HCID 131368767-[[2-(Acetylamino)-1-oxopropyl]-amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 62.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.93 g (30 mmol) of N-acetyl-L-alanine, 3.30 ml (30 mmol) of N-methyl morpholine, 2.33 ml (30 mmol) of methyl chloroformate, and 80 ml of acetonitrile is stirred at -10° to -20° for 30 minutes. A mixture of 4.08 g (20 mmol) of 7-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 8.4 ml (60 mmol) of triethylamine, 7.6 ml (60 mmol) of chlorotrimethylsilane, and 100 ml of dichloromethane is stirred at room temperature for 30 minutes and then cooled to -20°. The cold mixed anhydride is added to the cold silylated quinoline and stirred with cooling for 3 hours and overnight at room temperature. The reaction mixture is evaporated to dryness and the residue is treated with water. The solid is filtered to give 3.98 g of 7-[[2-(acetylamino)-1-oxopropyl]-amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.

Workup

  1. stirringis stirred at room temperature for 30 minutes
  2. temperaturecooled to -20°
  3. stirringstirred
  4. customThe reaction mixture is evaporated to dryness
  5. additionthe residue is treated with water
  6. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-f223e7d94c4c4fdab919dac0959f113f
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Linked notes

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