Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6) → HCID 178462122, compound

HRID 1944761Notes

Reaction equation

O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:11].[Mg+2].[F:21][C:22]1[CH:27]=[CH:26][C:25]([C@H:28]([NH:30][C:31]([C@H:33]2[CH2:38][CH2:37][C@H:36]([NH:39][S:40]([C:43]3[CH:48]=[CH:47][C:46]([C:49]4[CH:54]=[CH:53][N:52]=[CH:51][CH:50]=4)=[CH:45][CH:44]=3)(=[O:42])=[O:41])[CH2:35][CH2:34]2)=[O:32])[CH3:29])=[CH:24][CH:23]=1>CO.C(Cl)Cl>[F:21][C:22]1[CH:27]=[CH:26][C:25]([C@H:28]([NH:30][C:31]([C@H:33]2[CH2:34][CH2:35][C@H:36]([NH:39][S:40]([C:43]3[CH:44]=[CH:45][C:46]([C:49]4[CH:54]=[CH:53][N+:52]([O-:11])=[CH:51][CH:50]=4)=[CH:47][CH:48]=3)(=[O:41])=[O:42])[CH2:37][CH2:38]2)=[O:32])[CH3:29])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Magnesium monoperoxyphthalate hexahydrate (66.8 mg, 0.135 mmol) was suspended in MeOH (0.5 ml) and cooled to 0° C. Trans-4-(4-pyridin-4-yl-benzenesulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (Example 284, 50 mg, 0.097 mmol) in DCM (0.5 ml) was added dropwise and the reaction mixture was left to stir overnight at 23° C. LCMS indicated that the reaction was complete, and the mixture was concentrated in vacuo to a residue which was purified by reverse phase chromatography on prep-HPLC (150 mm, C8 luna, 15-20 min run, 10%-100% MeCN in water containing 0.1% TFA). Product containing fractions were lyophilized to yield the title compound (10 mg, 21%). MS MH+ 498.1

Workup

waitthe reaction mixture was left
concentrationthe mixture was concentrated in vacuo to a residue which
customwas purified by reverse phase chromatography on prep-HPLC (150 mm, C8 luna, 15-20 min run, 10%-100% MeCN in water containing 0.1% TFA)
additionProduct containing fractions

Sources & evidence

ORD record: ord-a6f8903403f6485a827fa5c54a352a46
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394858B2

Reaction notes

Loading…