Tetrabutylammonium Fluoride → tert-butyl (6R,7S)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022619Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@H:10]2[NH:23]C(OCC[Si](C)(C)C)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[NH2:23][C@H:10]1[C@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of tert-butyl (6R,7S)-7-(3,4-dichlorophenyl)-6-({[2-(trimethylsilyl)ethoxy]carbonyl}amino)-1,4-oxazepane-4-carboxylate (0.67 g) in THF (5 mL) was added tetra-n-butylammonium fluoride (5.2 mL) at room temperature, and the mixture was stirred at 50° C. for 5 hr. 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 to give the title compound (0.4 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

Sources & evidence

ORD record: ord-d6e176d3462449ba8bc9ed5b5e0861cd
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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