Pyridinium hydrobromide → tert-Butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate

HRID 1501319Notes

Reaction equation

[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BrH:28].[NH+]1C=CC=CC=1>C1COCC1>[Br:28][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1)=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of tert-butyl {1-[4-(phenylacetyl)phenyl]cyclobutyl}carbamate (5.0 g, 13.68 mmol, 1.0 eq) and pyridinium hydrobromide perbromide (4.38 g, 13.68 mmol, 1.0 eq) in THF (78 mL) was stirred at 0° C. for 30 minutes. The mixture was partitioned between EtOAc and water and the organic phase washed respectively with aqueous sodium thiosulfate solution and brine, dried, filtered through a silicone coated filter paper and concentrated in vacuo to give the crude title compound (5.44 g, 93% purity by UPLC-MS) which was used without further purification.

Workup

customThe mixture was partitioned between EtOAc and water
washthe organic phase washed respectively with aqueous sodium thiosulfate solution and brine
customdried
filtrationfiltered through a silicone coated filter paper
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fd6aca275a83463a9f5a963f98c0458c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206185B2

Reaction notes

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