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

HRID 851007

반응식

HRID 851007 반응식
[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]

참가 물질

8

반응물 6

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bbb0dffa458949ceaefef443213fc58e
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04382089

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