Water → HCID 66838914, compound

HRID 546682Notes

Reaction equation

[Cl-:1].[Li+].C1(C)C=CC(S([O:12][CH2:13][CH2:14][CH:15]([CH3:35])[CH:16]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:17]([NH:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:18])(=O)=O)=CC=1.O.C(OCC)(=O)C>CN(C=O)C>[Cl:1][CH:13]([OH:12])[CH2:14][CH:15]([CH3:35])[CH:16]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)[C:17]([NH:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

Lithium chloride (283 mg) was added to a solution of 5-(N′-tert-butoxycarbonylhydrazino)-4-(4-fluorophenyl)-3-methyl-5-oxo-1-pentyl toluene-4-sulfonate (330 mg) in DMF (5 mL). The reaction solution was stirred at 80° C. for three hours and then left to cool to room temperature. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 170 mg of the title compound. The property value of the compound is as follows.

Workup

waitleft
temperatureto cool to room temperature
customthe organic layer was separated
washThe resulting organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record: ord-974351a783c743489a159d6dd9141e37
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935815B2

Reaction notes

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