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 910766노트

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HRID 910766 반응식
[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]

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f4bb6faa5854453098cceb6a6c585a05
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022218B2

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