Triphenylphosphine → (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

HRID 910766ノート

反応式

HRID 910766 の反応式
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][OH:10])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[Br:14][C:15]1[CH:16]=[C:17]([C@H:25]2[C:34]3[C:33](=[O:35])[CH2:32][C@@H:31]([CH2:36][CH2:37][CH3:38])[CH2:30][C:29]=3[NH:28][C:27]([CH3:39])=[C:26]2[C:40]#[N:41])[CH:18]=[C:19]([O:22][CH2:23][CH3:24])[C:20]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Br:14][C:15]1[CH:16]=[C:17]([C@H:25]2[C:34]3[C:33](=[O:35])[CH2:32][C@@H:31]([CH2:36][CH2:37][CH3:38])[CH2:30][C:29]=3[NH:28][C:27]([CH3:39])=[C:26]2[C:40]#[N:41])[CH:18]=[C:19]([O:22][CH2:23][CH3:24])[C:20]=1[O:10][CH2:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([F:1])=[CH:3][C:4]=1[N+:11]([O-:13])=[O:12]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57475722(4,5-Difluoro-2-nitrophenyl)methanolHCID 67417503(4R,7S)-4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

生成物 1

HCID 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a mixture of (4,5-difluoro-2-nitro-phenyl)-methanol (Example 72f, 5.1 g), (4R,7S)-4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (Example 72e, 10.0 g) and polymer-supported triphenylphosphine (13.5 g, 3 mmol/g loading) in THF (500 ml), cooled to 0° C., was added diisopropyl azodicarboxylate (DIAD) (5.3 ml). After 1.5 h, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 4/1-2/3 (v/v) as eluent.

後処理

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 4/1-2/3 (v/v) as eluent

出典と根拠

ORDレコード
ord-f4bb6faa5854453098cceb6a6c585a05
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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