Triethylamine → tert-butyl (6S,7R)-6-cyano-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022719Notes

Reaction equation

[C:1]([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)(=O)[NH2:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[C:1]([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)#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl (6R,7R)-6-carbamoyl-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (437 mg) and triethylamine (0.344 ml) in THF (5.6 mL) was added trifluoroacetic anhydride (0.171 mL), and the mixture was stirred at 0° C. for 2 hr. Then, the mixture was stirred at room temperature for 1 hr, distilled water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (205 mg).

Workup

stirringThen, the mixture was stirred at room temperature for 1 hr
distillationdistilled water
additionwas added to the reaction mixture
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with distilled water and brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-41efa7c80a9e4f55987cfe04d6d68d65
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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