Cesium carbonate → Tert-butyl (4-methoxybutyl)(3-methoxy-2-nitrophenyl)carbamate

HRID 2168947Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([N+:17]([O-:19])=[O:18])=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.CS(O[CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:30][O:29][CH2:28][CH2:27][CH2:26][CH2:25][N:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[N+:17]([O-:19])=[O:18])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 65 °C

Procedure

tert-Butyl (3-methoxy-2-nitrophenyl)carbamate (3.00 g) and 4-methoxybutyl methanesulfonate (3.06 g) were dissolved in dimethylformamide (40 ml), cesium carbonate (7.30 g) was added, and the mixture was stirred at 65° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-hexane (5:95-7:3) was concentrated under reduced pressure to give the object product (2.11 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additiondiluted with water
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
washa fraction eluted with ethyl acetate-hexane (5:95-7:3)
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-3fb0bd213c654465954361b787e03b61
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045436B2

Reaction notes

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