Chlorotrimethylsilane → 6-[[(1-Acetyl-2-pyrrolidinyl)carbonyl]-amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid

HRID 850998

반응식

HRID 850998 반응식
[C:1]([N:4]1[CH2:11][CH2:10][CH2:9][C@H:5]1[C:6]([OH:8])=O)(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])[C:32]([C:39]([OH:41])=[O:40])=[CH:31]2.C(N(CC)CC)C.Cl[Si](C)(C)C.N1CCC[C@H]1C(O)=O>ClCCl>[C:1]([N:4]1[CH2:11][CH2:10][CH2:9][CH:5]1[C:6]([NH:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])[C:32]([C:39]([OH:41])=[O:40])=[CH:31]2)=[O:8])(=[O:3])[CH3:2]

참가 물질

9

반응물 7

HCID 6397ChlorotrimethylsilaneHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 66141N-Acetyl-L-prolineHCID 145742L-ProlineHCID 131063306-Amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

생성물 1

HCID 131368646-[[(1-Acetyl-2-pyrrolidinyl)carbonyl]-amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid수율 64.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 4.71 g (30 mmol) of N-acetyl-L-proline and 60 ml of dichloromethane is cooled to -18° and 3.3 ml (30 mmol) of N-methyl morpholine and 3.9 ml (30 mmol) of isobutyl chloroformate is added, and the reaction mixture is stirred for 30 minutes at -10° to -20°. A mixture of 4.08 g (20 mmol) of 6-amino-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid, 150 ml of dichloromethane, 8.4 ml (60 mmol) of triethylamine, and 7.6 ml (60 mmol) of chlorotrimethylsilane is stirred at room temperature for 35 minutes. The silylation mixture is cooled to -20° and the mixed anhydride of proline is added and stirred with cooling overnight. The reaction mixture is evaporated to dryness, and the residue is treated with ethanol to yield 4.42 g of 6-[[(1-acetyl-2-pyrrolidinyl)carbonyl]-amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid, mp 303° dec.

후처리

  1. stirringis stirred at room temperature for 35 minutes
  2. temperatureThe silylation mixture is cooled to -20°
  3. stirringstirred
  4. temperaturewith cooling overnight
  5. customThe reaction mixture is evaporated to dryness
  6. additionthe residue is treated with ethanol

출처 및 근거

ORD 기록
ord-f517b170a6ef4c969b8511f3ac9afc36
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04382089

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