Ethyl Acetate → 1-(2,4-Difluorophenyl)-6-fluoro-1,4-dihydro7-(5((5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl)-2,5diazabicyclo(2.2.1)-hept-2-yl)-4-oxoquinoline-3-carboxylic acid

HRID 727941

反応式

HRID 727941 の反応式
O.[CH:2]12[CH2:8][CH:5]([NH:6][CH2:7]1)[CH2:4][N:3]2[C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:30])[C:14]([C:27]([OH:29])=[O:28])=[CH:15][N:16]2[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])=[CH:11][C:10]=1[F:31].C(=O)(O)[O-].[Ca+2].C(=O)(O)[O-].Br[CH2:42][C:43]1[O:44][C:45](=[O:49])[O:46][C:47]=1[CH3:48].C(OCC)(=O)C>CN(C=O)C.O>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[N:16]1[C:17]2[C:12](=[CH:11][C:10]([F:31])=[C:9]([N:3]3[CH2:4][CH:5]4[CH2:8][CH:2]3[CH2:7][N:6]4[CH2:42][C:43]3[O:44][C:45](=[O:49])[O:46][C:47]=3[CH3:48])[CH:18]=2)[C:13](=[O:30])[C:14]([C:27]([OH:29])=[O:28])=[CH:15]1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10176262Calcium bicarbonateHCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-oneHCID 67927890HCID 67927890、化合物

生成物 1

HCID 140148351-(2,4-Difluorophenyl)-6-fluoro-1,4-dihydro7-(5((5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl)-2,5diazabicyclo(2.2.1)-hept-2-yl)-4-oxoquinoline-3-carboxylic acid収率 27.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To 188 mg (0.434 m Mol) of 7-(2,5-diazabicyclo(2.2.1)hept-2-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-di-hydro-4-oxoquinoline-3-carboxylic acid monohydrate (Example 11) was suspended in 20 ml dry DMF was added 96 mg (0.95 m Mol) anhydrous calcium bicarbonate and 92 mg (0.48 m Mol) 4-bromomethyl-5-methyl-1,3-dioxolen-2-one. The resultant suspension was stirred at room temperature for 10 hrs. Then the suspension was treated with 150 ml of ethyl acetate and 50 ml of water. The organic phase was separated and washed with 5×30 ml water, dried over sodium sulfate, filtered the volatiles were removed at room temperature under reduced pressure. Recrystallization from ethyl acetate gave 63 mg (27.5%) of the desired material.

後処理

  1. customThe organic phase was separated
  2. washwashed with 5×30 ml water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered the volatiles
  5. customwere removed at room temperature under reduced pressure
  6. customRecrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-91c076c09db74192bcdea3de1c3ea8e2
出典データセット
uspto-grants-1991_09
特許番号
US05045549

関連ノート

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