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 910767Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-2442a472801443f0bbffb794e9e93785
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022218B2

Reaction notes

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