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 910767노트

반응식

HRID 910767 반응식
[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]

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2442a472801443f0bbffb794e9e93785
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022218B2

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