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

HRID 564527Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:22])[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:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]2[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@@H:32]([CH3:43])[CH2:31]2)[CH:24]=1.O[Li].O.CC(O)=O>CO.O>[CH3:42][C:39]([O:38][C:36]([N:33]1[CH2:34][CH2:35][N:30]([CH2:29][C:25]2[CH:24]=[C:23]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[C:5]([CH2:8][N:9]([CH3:22])[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:28]=[CH:27][CH:26]=2)[CH2:31][C@@H:32]1[CH3:43])=[O:37])([CH3:40])[CH3:41]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1,1-dimethylethyl (2S)-4-[(2′-fluoro-5′-{[methyl({3-[(methyloxy)carbonyl]phenyl}carbonyl)amino]methyl}-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate (0.215 g, 0.365 mmol) in MeOH/H2O (1.0/0.5 mL) was added LiOH.H2O (0.077 g, 1.83 mmol). The mixture was heated with a microwave at 80° C. for 30 min. Then it was acidified with HOAc. This mixture was extracted with DCM which was dried over Na2SO4, filtered, concentrated and purified using a Gilson HPLC to afford the title compound 0.0639 g (30%). LC-MS m/z 576 (M+H)+.

Workup

extractionThis mixture was extracted with DCM which
dry with materialwas dried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified

Sources & evidence

ORD record: ord-06298f3f776944479e1950c73e3a242e
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067408B2

Reaction notes

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