Dimethylformamide → HCID 57860518, compound

HRID 1947136Notes

Reaction equation

[CH2:1]([N:3]([CH2:24][CH3:25])[CH2:4][CH2:5][N:6]([CH3:23])[C:7]([C:9]1[S:17][C:16]2[CH:15]=[C:14]([CH3:18])[NH:13][C:12](=[O:19])[C:11]=2[C:10]=1[O:20][CH2:21][CH3:22])=[O:8])[CH3:2].[CH2:26](Br)[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:24]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]([CH3:23])[C:7]([C:9]1[S:17][C:16]2[CH:15]=[C:14]([CH3:18])[N:13]([CH2:26][C:27](=[O:28])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:12](=[O:19])[C:11]=2[C:10]=1[O:20][CH2:21][CH3:22])=[O:8])[CH3:25]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the compound of Example 145 (300 mg, 0.821 mmol), phenacyl bromide (196 mg, 0.985 mmol), potassium carbonate (272 mg, 1.97 mmol) and DMF (5 mL) was stirred at 60° C. for 15 hr. After cooling, the mixture was diluted with water (10 mL), and extracted with ethyl acetate. The extract was washed successively with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=1/9 to 10/0) to give the title compound (51.2 mg, 13%) as a colorless oil.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washThe extract was washed successively with water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=1/9 to 10/0)

Sources & evidence

ORD record: ord-5af6d2c3432148f68265d00de16e24b5
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399449B2

Reaction notes

Loading…