tert-Butanol → 3-Nitro-5-(octadecyloxy)phenylcarbamic acid dimethylethyl ester
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:12]=1)C(O)=O)([O-:3])=[O:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1.C([N:51]([CH2:54]C)CC)C.[C:56]([OH:60])([CH3:59])([CH3:58])[CH3:57]>>[CH3:57][C:56]([O:60][C:54](=[O:39])[NH:51][C:6]1[CH:10]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:59])[CH3:58]Participants
5
Procedure
A mixture of 5.0 g (11.5 mmol) of 3-nitro-5-(octadecyloxy)benzoic acid, 3.0ml (13.8 mmol) of diphenylphosphoryl azide and 2.0 ml (13.8 mmol) of triethylamine in 45 ml of t-butylalcohol (freshly distilled from sodium) was stirred at reflux under argon for 20 hours. The excess t-butylalcohol was removed at reduced pressure and methylene chloride was added to the residue. The extract was washed with NaHCO3 solution, dried and concentrated at reduced pressure to an oil which was purified by HPLC using 5% ethyl acetate-hexane to give 4.6 g (79% yield, mp 70°-72°) of 3-nitro-5-(octadecyloxy)phenylcarbamic acid dimethylethyl ester. The structure was confirmed by nmr and mass spectra.
Workup
- distillationfreshly distilled from sodium)
- temperatureat reflux under argon for 20 hours
- customThe excess t-butylalcohol was removed at reduced pressure and methylene chloride
- additionwas added to the residue
- washThe extract was washed with NaHCO3 solution
- customdried
- concentrationconcentrated at reduced pressure to an oil which
- customwas purified by HPLC
Sources & evidence
- ORD record
- ord-6a4f31d19040426daddf800bbfa932c2
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05446189
Reaction notes
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