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1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(cis-3-Amino-4-methyl-1-pyrrolidinyl)-8-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580587
ノート
印刷プレビュー

反応式

HRID 580587 の反応式
[Br:1][C:2]1[C:3](F)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].C(OC([NH:28][C@H:29]1[C@@H:33]([CH3:34])[CH2:32][NH:31][CH2:30]1)=O)(C)(C)C.C1CCN2C(=NCCC2)CC1>C(#N)C>[NH2:28][C@H:29]1[C@@H:33]([CH3:34])[CH2:32][N:31]([C:3]2[C:2]([Br:1])=[C:11]3[C:6]([C:7](=[O:18])[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]3[CH:12]3[CH2:14][CH2:13]3)=[CH:5][C:4]=2[F:19])[CH2:30]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11138119(3S,4S)-3-(Boc-amino)-4-methylpyrrolidineHCID 137488068-Bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

生成物 1

HCID 703541507-(cis-3-Amino-4-methyl-1-pyrrolidinyl)-8-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid収率 25.6%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

A mixture of 8-bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.19 g), cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.14 g), DBU (0.095 g) and anhydrous acetonitrile (5 ml) was refluxed for 2 hours and then concentrated. The resulting residue was dissolved in chloroform (70 ml), washed with 10% aqueous citric acid solution, water successively, dried over anhydrous sodium sulfate and then concentrated. To the resulting oily residue was added hot methanol to crystallize and cooled. The resulting precipitate was collected by filtration, added to the mixture of concentrated hydrochloric acid-methanol (1:1, 3 ml) and stirred for 2.5 hours under elevated temperature. The reaction mixture was neutralized with concentrated aqueous ammonia, the resulting precipitate was collected by filtration, washed with ice-water and recrystallized from dichloromethane-methanol-concentrated aqueous ammonia (10:10:1) to give the title compound (0.06 g) as yellow prisms, mp 225°-226.5° C. (decompd.).

後処理

  1. temperaturewas refluxed for 2 hours
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in chloroform (70 ml)
  4. washwashed with 10% aqueous citric acid solution, water successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. additionTo the resulting oily residue was added hot methanol
  8. customto crystallize
  9. temperaturecooled
  10. filtrationThe resulting precipitate was collected by filtration
  11. additionadded to the mixture of concentrated hydrochloric acid-methanol (1:1, 3 ml)
  12. filtrationthe resulting precipitate was collected by filtration
  13. washwashed with ice-water
  14. customrecrystallized from dichloromethane-methanol-concentrated aqueous ammonia (10:10:1)

出典と根拠

ORDレコード
ord-044fb902b5d442b0981969a9b1580ca0
出典データセット
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04753953

反応ノート

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