Dimethylformamide → HCID 21072941, compound

HRID 1373257Notes

Reaction equation

[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[NH2:25])[CH:12]=1)([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].Br[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]([O:5][C:6]([NH:7][C:8]([C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[NH:25][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])([CH3:10])[CH3:9])=[O:26])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl[1-[3-(2-amino-5-chlorophenoxy)phenyl]-1-methylethyl]carbamate (2.5 g, 6.62 mmols), ethyl 4-bromobutyrate (9.0 g, 46 mmols), potassium carbonate (2.7 g, 20 mmols) and N,N-dimethylformamide (20 ml) was stirred at 80° C. for 24 hours. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to give an oil of ethyl 4-[N-[2-[3-(1-tert-butoxycarbonylamino-1-methylethyl)phenoxy]-4-chlorophenyl]]aminobutyrate (1.6 g, 49%).

Workup

temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialdried with anhydrous magnesium sulfate
concentrationThis was concentrated under reduced pressure
customthe residue was purified through silica gel column chromatography

Sources & evidence

ORD record: ord-e952d7fb54894bb78fae390ce05c7cfd
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07160887B1

Reaction notes

Loading…