Boron trifluoride etherate → HCID 11464532, compound

HRID 1019336Notes

Reaction equation

[CH2:1]([N:8]1[CH:15](O)[C@H:14]2[N:10]([C@H:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:12][CH2:13]2)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)O[C:27]1([CH:34]=[CH:33][CH:32]=[CH:31][CH2:30]1)[CH:28]=[CH2:29].B(F)(F)F.CC[O:43]CC>ClCCl.CCOCC>[CH2:1]([N:8]1[C@@H:15]([CH2:29][C:28]([C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:43])[C@H:14]2[N:10]([C@H:11]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[S:12][CH2:13]2)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of compound 6-benzyl-7-hydroxy-3-phenyl-(3S, 7aR)-perhydroimidazo[1,5-C][1,3]thiazol-5-one of formula (6) (0.326 parts, 1 mmol) in dichloromethane (10 parts) was added 1-trimethylsilyloxy styrene (0.384 parts, 2 mmol). Then the solution was cooled to 0° C, and Lewis acid for example borontrifluoride etherate (BF3.Et2O) (0.142 parts, 1 mmol) was added drop wise. The reaction mixture was stirred at 0° C. for 10 mints, and the reaction mixture was quenched with saturated ammonium chloride (10 parts). Then the organic layer was separated, concentrated and column purification with ethylacetate:pet.ether (15:85) as eluent provided compound 2-[6-benzyl-5-oxo-3-phenyl-(3S, 7S, 7aR)-perhydroimidazo[1,5-C][1,3]thiazol-7-yl]-1-phenyl-1-ethanone of formula (7a) (viscous liquid, 0.419 parts, 0.98 mmol) in 98% yield.

Workup

customthe reaction mixture was quenched with saturated ammonium chloride (10 parts)
customThen the organic layer was separated
concentrationconcentrated
customcolumn purification with ethylacetate

Sources & evidence

ORD record: ord-cce70c0aadf04f60be5ece43a78adc9a
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06486328B1

Reaction notes

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