Chlorotrimethylsilane → 8-[[2-(Acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 851008

반응식

HRID 851008 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:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[NH:31][CH:30]=[C:29]([C:33]([OH:35])=[O:34])[C:28]2=[O:36].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:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[NH:31][CH:30]=[C:29]([C:33]([OH:35])=[O:34])[C:28]2=[O:36])=[O:9])(=[O:3])[CH3:2]

참가 물질

9

반응물 6

HCID 6397ChlorotrimethylsilaneHCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 88064N-Acetyl-L-alanineHCID 128663498-Amino-4-hydroxyquinoline-3-carboxylic acid

생성물 1

HCID 131368788-[[2-(Acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid수율 47.7%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 3.93 g (30 mmol) of N-acetyl-L-alanine, 3.3 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 8-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 was stirred at room temperature for 40 minutes and then cooled to -20°. The cold mixed anhydride is added to the cold silylated quinoline and stirred for 4 hours with cooling and overnight at room temperature. The reaction mixture is evaporated to dryness and the residue is treated with acetonitrile and 1N hydrochloric acid. The solid is filtered to give 3.03 g of 8-[[2-(acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4 -oxo-3-quinolinecarboxylic acid.

후처리

  1. stirringwas stirred at room temperature for 40 minutes
  2. temperaturecooled to -20°
  3. stirringstirred for 4 hours
  4. customThe reaction mixture is evaporated to dryness
  5. additionthe residue is treated with acetonitrile and 1N hydrochloric acid
  6. filtrationThe solid is filtered

출처 및 근거

ORD 기록
ord-aefc5b7aaa064d9894f82adf7b1a2ce8
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04382089

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