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

HRID 580596
ノート
印刷プレビュー

反応式

HRID 580596 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 137488068-Bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidHCID 53686699rac-tert-butyl N-[(3R,4S)-4-methylpyrrolidin-3-yl]carbamate

生成物 1

HCID 703533807-(trans-3-Amino-4-methyl-1-pyrrolidinyl)-8-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid収率 29.5%

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 (0.11 g), trans-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.082 g), DBU (0.054 g) and anhydrous acetonitrile (5 ml) was refluxed for 1.5 hours and then concentrated. The resulting residue was dissolved in chloroform (50 ml) and washed with 10% aqueous citric acid solution and water successively. The organic layer was concentrated under reduced pressure and to the oily residue was added methanol to crystallize. The resulting precipitate was collected by filtration, washed with chilled methanol and this was added to concentrated hydrochloric acid-methanol (1:1, 2 ml) and stirred for an hour at room temperature. The reacting mixture was neutralized with concentrated aqueous ammonia, concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform:methanol:concentrated aqueous ammonia=20:6:1) and then recrystallized from dichloromethanemethanol (1:1) to give the title compound (0.04 g) as pale yellow powder, mp 186°-190° C. (decompd.).

後処理

  1. temperaturewas refluxed for 1.5 hours
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in chloroform (50 ml)
  4. washwashed with 10% aqueous citric acid solution and water successively
  5. concentrationThe organic layer was concentrated under reduced pressure and to the oily residue
  6. additionwas added methanol
  7. customto crystallize
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with chilled methanol
  10. additionthis was added to concentrated hydrochloric acid-methanol (1:1, 2 ml)
  11. concentrationconcentrated under reduced pressure
  12. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol:concentrated aqueous ammonia=20:6:1)
  13. customrecrystallized from dichloromethanemethanol (1:1)

出典と根拠

ORDレコード
ord-2ba97b3bfde54e4db132c7fd7abc1202
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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