Water → HCID 66839189, compound

HRID 546690Notes

Reaction equation

[Cl-:1].[Li+].C1(C)C=CC(S(O[CH2:13][CH:14]([OH:37])[CH2:15][CH:16]([C:28]2[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[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][CH2:13][CH:14]([OH:37])[CH2:15][CH:16]([C:28]1[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[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 (818 mg) was added to a solution of 5-(N′-tert-butoxycarbonylhydrazino)-2-hydroxy-5-oxo-4-(3,4,5-trifluorophenyl)pentyl toluene-4-sulfonate (1.03 g) in DMF (8 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, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 734 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-7adae3683df64ccdb1886343c9b8ce6a
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935815B2

Reaction notes

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