Hydrochloric Acid → HCID 14180962, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.C(Cl)(=O)C(C)(C)C.Cl.[N+:21]([C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29][NH2:30])=[CH:26][CH:25]=1)([O-:23])=[O:22].Cl>C1COCC1.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([NH:30][CH2:29][CH2:28][C:27]2[CH:26]=[CH:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:32][CH:31]=2)=[O:12])=[CH:7][CH:8]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 4-methoxybenzeneacetic acid (8.3 g) in dry THF (250 ml) was treated with triethylamine (6.9 ml) and wooled in a salt/ice-bath with stirring under a nitrogen atmosphere. Pivaloyl chloride (6.1 ml) was added and stirring continued for 1 h. A further aliquot of triethylamine (6.9 ml) was added followed by p-nitrophenethylamine hydrochloride (10 g). The resultant suspension was warmed to room temperature and stirred for 19.5 h (overnight). The reaction mixture was acidified to pH 1 using hydrochloric acid solution (2N; 30 ml) and the resultant solution was extracted with EA (1×250 ml, 1×100 ml). The combined organic extracts were washed with 8% NaHCO3 solution (200 ml), dried (MgSO4) and evaporated under reduced pressure to give a brown oil. Purification by `flash` chromatography, ER:CH2Cl2 (4:1) gave the title compound as a pale yellow solid (7.4 g) m.p. 109°-110°.
Workup
- stirringstirring
- stirringstirred for 19.5 h (overnight)
- extractionthe resultant solution was extracted with EA (1×250 ml, 1×100 ml)
- washThe combined organic extracts were washed with 8% NaHCO3 solution (200 ml)
- dry with materialdried (MgSO4)
- customevaporated under reduced pressure
- customto give a brown oil
- customPurification by `flash` chromatography, ER
Sources & evidence
- ORD record
- ord-53ac06e184ac42fab9b47170c5f00ad0
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04855314
Reaction notes
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