1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(cis-3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 580590ノート

反応式

HRID 580590 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([CH2:14][CH2:15][F:16])[CH:7]=[C:6]([C:17]([OH:19])=[O:18])[C:5]2=[O:20].[C:21]([O:25][C:26]([NH:28][C@H:29]1[C@@H:33]([CH3:34])[CH2:32][NH:31][CH2:30]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C1CCN2C(=NCCC2)CC1>C(#N)C>[C:21]([O:25][C:26]([NH:28][C@H:29]1[C@@H:33]([CH3:34])[CH2:32][N:31]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:20])[C:6]([C:17]([OH:19])=[O:18])=[CH:7][N:8]3[CH2:14][CH2:15][F:16])=[CH:3][C:2]=2[F:1])[CH2:30]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

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 127709081-(2-Fluoroethyl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

生成物 1

HCID 867422497-(cis-3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid収率 62.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 6,7,8-trifluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), anhydrous acetonitrile (5 ml), cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (0.5 g) and DBU (0.27 g) was refluxed for an hour and then concentrated. The resulting residue was dissolved in chloroform and the solution was washed with 10% aqueous citric acid solution. After concentration of the chloroform layer, the resulting precipitate was triturated in water, and collected by filtration and washed with water, methanol and ether successively to give the title compound (0.51 g) as white powder, mp 217°-219° C.

後処理

  1. temperaturewas refluxed for an hour
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in chloroform
  4. washthe solution was washed with 10% aqueous citric acid solution
  5. customAfter concentration of the chloroform layer, the resulting precipitate was triturated in water
  6. filtrationcollected by filtration
  7. washwashed with water, methanol and ether successively

出典と根拠

ORDレコード
ord-c6b8985c7fac49b795c3d29364acab73
出典データセット
uspto-grants-1988_06
特許番号
US04753953

反応ノート

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