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

HRID 851005

反応式

HRID 851005 の反応式
[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]

参加物

9

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f223e7d94c4c4fdab919dac0959f113f
出典データセット
uspto-grants-1983_05
特許番号
US04382089

関連ノート

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