Phenethyl bromide → HCID 9888561, compound

HRID 1830820Notes

Reaction equation

[NH2:1][C:2]1[C:19]([CH3:20])=[C:18]([CH3:21])[C:5]([O:6][CH2:7][C:8]([N:10]([CH3:17])[CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:9])=[C:4]([CH3:22])[C:3]=1[CH3:23].[CH2:24](Br)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(#N)C>[NH2:1][C:2]1[C:19]([CH3:20])=[C:18]([CH3:21])[C:5]([O:6][CH2:7][C:8]([N:10]([CH3:17])[CH:11]2[CH2:16][CH2:15][N:14]([CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:13][CH2:12]2)=[O:9])=[C:4]([CH3:22])[C:3]=1[CH3:23]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture solution of 99 mg of the compound (1) obtained in the Example 1 and 42.3 μl of phenethyl bromide in 2 ml of acetonitrile was added 65 μl of triethylamine, and the mixture was stirred for 5 hours at 60° C. After the reaction, saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saline, dried and concentrated under reduced pressure to give the residue. The obtained residue was purified by amine-coated silica gel (Fuji Silysia Chemical Ltd.) column chromatography (dichloromethane : ether =1:1) to give 86 mg (65%) of the above-mentioned compound (6).

Workup

additionwas added to the reaction mixture
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saline
customdried
concentrationconcentrated under reduced pressure
customto give the residue
customThe obtained residue was purified by amine-coated silica gel (Fuji Silysia Chemical Ltd.) column chromatography (dichloromethane : ether =1:1)

Sources & evidence

ORD record: ord-62d3eecd5a02491db7cec4d7f5cbf10c
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067533B2

Reaction notes

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