1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 76831218, compound

HRID 1186163Notes

Reaction equation

N12CCCN=C1CCCCC2.[CH2:12]([O:15][C:16](=[O:26])[CH2:17][C:18]1[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:19]=1[F:25])[CH:13]=[CH2:14].C(NC1C=CC(S([N:40]=[N+:41]=[N-])(=O)=O)=CC=1)(=O)C>C1COCC1>[CH2:12]([O:15][C:16](=[O:26])[C:17]([C:18]1[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:19]=1[F:25])=[N+:40]=[N-:41])[CH:13]=[CH2:14]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (4.2 ml, 28 mmol) in THF (24 ml) at 23° C. was added a solution of (5-bromo-2-fluoro-phenyl)-acetic acid allyl ester (intermediate B3A) (7.29 g, 27 mmol) and commercially available p-acetamidobenzenesulfonyl azide ([CAS No. 2158-14-7], 6.94 g, 28 mmol) in THF (48 ml) over 1 h. The mixture was stirred for 5 h at 23° C. Then it was quenched with sat. aqueous ammonium chloride solution, diluted with ethyl acetate, and the organic layer was washed with brine and dried over sodium sulfate. Removal of the solvent in vacuum left a yellow oil, which was purified by silica gel column chromatography with hexane/ethyl acetate to give the title compound as a yellow solid (7.344 g, 92%). MS (ISP): m/z=316.1 [(M+NH4)+] and 318.0 [(M+2+NH4)+].

Workup

customThen it was quenched with sat. aqueous ammonium chloride solution
additiondiluted with ethyl acetate
washthe organic layer was washed with brine
dry with materialdried over sodium sulfate
customRemoval of the solvent in vacuum
waitleft a yellow oil, which
customwas purified by silica gel column chromatography with hexane/ethyl acetate

Sources & evidence

ORD record: ord-eb7c45a62350436590fcf24dbc9e9407
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673894B2

Reaction notes

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