Dimethylformamide → 1,4-Dihydro-4-oxo-8-[[(5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-quinolinecarboxylic acid

HRID 851007

反応式

HRID 851007 の反応式
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][CH2:3]1.S(Cl)(Cl)=O.CN(C)C=O.[NH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[NH:28][CH:27]=[C:26]([C:30]([OH:32])=[O:31])[C:25]2=[O:33].C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl>[O:33]=[C:25]1[C:24]2[C:29](=[C:20]([NH:19][C:7]([CH:5]3[CH2:4][CH2:3][C:2](=[O:1])[NH:6]3)=[O:9])[CH:21]=[CH:22][CH:23]=2)[NH:28][CH:27]=[C:26]1[C:30]([OH:32])=[O:31]

参加物

8

反応物 6

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 7405L-Pyroglutamic AcidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 128663498-Amino-4-hydroxyquinoline-3-carboxylic acid

生成物 1

HCID 131368721,4-Dihydro-4-oxo-8-[[(5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-quinolinecarboxylic acid収率 53.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 3.87 g (30 mmol) of 5-oxo-L-proline, 2.19 ml (30 mmol) of thionyl chloride, 2.32 ml (30 mmol) of dimethylformamide, and 75 ml of dichloromethane is stirred with cooling for 1 hour. A mixture of 4.08 g (20 mmol) 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 is stirred at room temperature for 40 minutes and then is cooled to 0°. The cold acid chloride solution is added to the cold silylated quinoline and the mixture is stirred with cooling for 4 hours and at room temperature overnight. The reaction mixture is evaporated to dryness and the residue is treated with ethanol to give 3.40 g of 1,4-dihydro-4-oxo-8-[[(5-oxo-2-pyrrolidinyl)carbonyl]amino]-3-quinolinecarboxylic acid.

後処理

  1. temperaturewith cooling for 1 hour
  2. stirringis stirred at room temperature for 40 minutes
  3. temperatureis cooled to 0°
  4. stirringthe mixture is stirred
  5. customThe reaction mixture is evaporated to dryness
  6. additionthe residue is treated with ethanol

出典と根拠

ORDレコード
ord-bbb0dffa458949ceaefef443213fc58e
出典データセット
uspto-grants-1983_05
特許番号
US04382089

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