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

HRID 851005

반응식

HRID 851005 반응식
[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]

참가 물질

9

반응물 6

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f223e7d94c4c4fdab919dac0959f113f
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04382089

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