Water → tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(3-hydroxypent-1,4-dien-3-yl)-1,4-oxazepane-4-carboxylate

HRID 1022808Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([C:16](OC)=[O:17])[O:14][CH2:13][CH2:12][N:11]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:27]([Mg]Br)=[CH2:28].[CH2:31]1COC[CH2:32]1.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([C:16]([OH:17])([CH:27]=[CH2:28])[CH:31]=[CH2:32])[O:14][CH2:13][CH2:12][N:11]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-tert-butyl 7-methyl (6R,7R)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4,7-dicarboxylate (2.86 g) in THF (30 mL) was added 1.0 M vinylmagnesium bromide/THF solution (15.6 ml) under ice-cooling. The mixture was stirred at 0° C. for 20 min under nitrogen purging, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%)) to give the title compound (2.31 g) as a colorless oil.

Workup

temperaturecooling
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-50%))

Sources & evidence

ORD record: ord-1382898bd28248b1a729ee2155e8deaf
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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