Acetic Acid → (4R,7S)-4-[4-(2-Amino-4,5-difluoro-benzyloxy)-3-bromo-5-ethoxy-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

HRID 910767ノート

反応式

HRID 910767 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C@H:24]2[C:33]3[C:32](=[O:34])[CH2:31][C@@H:30]([CH2:35][CH2:36][CH3:37])[CH2:29][C:28]=3[NH:27][C:26]([CH3:38])=[C:25]2[C:39]#[N:40])[CH:5]=[C:6]([O:21][CH2:22][CH3:23])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[CH:12][C:11]=1[N+:18]([O-])=O.C(O)(=O)C>C1COCC1.[Zn]>[NH2:18][C:11]1[CH:12]=[C:13]([F:17])[C:14]([F:16])=[CH:15][C:10]=1[CH2:9][O:8][C:7]1[C:6]([O:21][CH2:22][CH3:23])=[CH:5][C:4]([C@H:24]2[C:33]3[C:32](=[O:34])[CH2:31][C@@H:30]([CH2:35][CH2:36][CH3:37])[CH2:29][C:28]=3[NH:27][C:26]([CH3:38])=[C:25]2[C:39]#[N:40])=[CH:3][C:2]=1[Br:1]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 67417478(4R,7S)-4-[3-Bromo-4-(4,5-difluoro-2-nitro-benzyloxy)-5-ethoxy-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

生成物 1

HCID 67417365(4R,7S)-4-[4-(2-Amino-4,5-difluoro-benzyloxy)-3-bromo-5-ethoxy-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of (4R,7S)-4-[3-Bromo-4-(4,5-difluoro-2-nitro-benzyloxy)-5-ethoxy-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (Example 72 g, 10.6 g) and acetic acid (19.6 ml) in THF (400 ml) was cooled to 0° C. Zinc dust (27.6 g) was added in portions under vigorous stirring. The mixture was stirred for 2 h at 0° C. and then filtered. The solids were washed with dichloromethane and the combined filtrates were washed with sat. aq. NaHCO3. The organic layer was dried (MgSO4), filtered and concentrated in vacuo.

後処理

  1. customwas cooled to 0° C
  2. filtrationfiltered
  3. washThe solids were washed with dichloromethane
  4. washthe combined filtrates were washed with sat. aq. NaHCO3
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2442a472801443f0bbffb794e9e93785
出典データセット
uspto-grants-2011_09
特許番号
US08022218B2

反応ノート

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