Water → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-1,4-oxazepane-4-carboxylate

HRID 1022708Notes

Reaction equation

[NH2:1][C:2](=[N:26][OH:27])[CH2:3][C@H:4]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[O:9][CH2:8][CH2:7][N:6]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5]1.[CH3:28][C:29](C)([O-])C.[K+].C(OCC)(=O)C.O>C1(C)C=CC=CC=1>[Cl:18][C:13]1[CH:12]=[C:11]([C@@H:10]2[O:9][CH2:8][CH2:7][N:6]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:5][C@H:4]2[CH2:3][C:2]2[N:1]=[C:28]([CH3:29])[O:27][N:26]=2)[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl (6R,7R)-6-[2-amino-2-(hydroxyimino)ethyl]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (388 mg, 0.93 mmol) in toluene (4 mL) were added potassium tert-butoxide (208 mg, 1.86 mmol) and ethyl acetate (1 mL, 0.93 mmol). The reaction mixture was stirred at 100° C. overnight. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (183.4 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-8a01925d028f401f8bd52d60c27b241f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

Loading…