[H-].[Na+].[OH:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])=[CH:6][CH:5]=1.[CH3:19][CH:20](Br)[CH2:21][CH3:22].O>O1CCCC1.CN(C=O)C>[CH3:19][CH:20]([O:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][NH:11][C:12](=[O:16])[O:13][CH2:14][CH3:15])=[CH:17][CH:18]=1)[CH2:21][CH3:22]To pre-washed sodium hydride (0.106 g, 4.4 mmol) in 5 ml of tetrahydrofuran (THF) and 5 ml of DMF at RT is added ethyl N-{2-(4-hydroxyphenoxy]ethyl}carbamate (1.0 g, 4.4 mmol) in 5 ml of THF. The mixture is stirred at RT for 1.5 hours and is then cooled to -5°. 1-Methylpropyl bromide (0.72 g, 5.3 mmol) in 2 ml of THF is added to the mixture, followed by addition of 5 ml of DMF. The reaction mixture is allowed to warm slowly to RT, and is then heated at 60° for 18 hours. The reaction is cooled to RT and poured into water and the mixture is extracted with ether (3×). The combined ether layers are washed with water until neutral, followed with brine, and dried over calcium sulfate. The solvent is removed in vacuo and purification by prep. TLC yields ethyl N-{2-[4-(1-methylpropoxy)phenoxy]ethyl}carbamate (compound 13, Table A).
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