Hydrochloric Acid → 3-{[({3'-[(4-{[(1,1-Dimethylethyl)oxy]carbonyl}-1-piperazinyl)methyl]-6-fluoro-3-biphenylyl}methyl)amino]carbonyl}benzoic Acid

HRID 564514Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([O:20]C)=[O:19])[CH:13]=2)=[O:11])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]2[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]2)[CH:23]=1.O[Li].O.Cl>CO.O>[CH3:41][C:38]([O:37][C:35]([N:32]1[CH2:31][CH2:30][N:29]([CH2:28][C:24]2[CH:23]=[C:22]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[C:5]([CH2:8][NH:9][C:10]([C:12]4[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=4)[C:18]([OH:20])=[O:19])=[O:11])[CH:4]=3)[CH:27]=[CH:26][CH:25]=2)[CH2:34][CH2:33]1)=[O:36])([CH3:39])[CH3:40]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1,1-dimethylethyl 4-[(2′-fluoro-5′-{[({3-[(methyloxy)carbonyl]phenyl}carbonyl)amino]methyl}-3-biphenylyl)methyl]-1-piperazinecarboxylate (0.26 g, 0.463 mmol) in MeOH/H2O (2/1 mL) was added LiOH.H2O (0.0971 g, 2.32 mmol). The mixture was heated with a microwave at 80° C. for 30 min. Then HCl was added to adjust the pH to ˜5. Then solvents were removed. The residue was extracted with DCM to afford the title compound 0.256 g (100%). LC-MS m/z 548 (M+H)+.

Workup

customThen solvents were removed
extractionThe residue was extracted with DCM

Sources & evidence

ORD record: ord-23d5aaa864854f9481fbac550ff280c0
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067408B2

Reaction notes

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