4,5-Difluorophthalic Anhydride → HCID 66975894, compound

HRID 1022694Notes

Reaction equation

[NH2:1][CH2:2][C@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1.[F:25][C:26]1[C:36]([F:37])=[CH:35][C:29]2[C:30](=[O:34])[O:31][C:32](=[O:33])[C:28]=2[CH:27]=1>CN(C=O)C.C(OCC)(=O)C>[C:21]([O:20][C:18]([N:5]1[CH2:4][C@@H:3]([CH2:2][NH:1][C:30]([C:29]2[CH:35]=[C:36]([F:37])[C:26]([F:25])=[CH:27][C:28]=2[C:32]([OH:33])=[O:31])=[O:34])[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[O:8][CH2:7][CH2:6]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl (6R,7R)-6-(aminomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (100 mg) in DMF (2 mL) was added 5,6-difluoro-2-benzofuran-1,3-dione (73.6 mg) at room temperature, and the mixture was stirred at 80° C. overnight. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (102 mg).

Workup

washThe diluted solution was washed with distilled water and brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-cd4dfd66351a406e8a6be2f78fe77899
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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