Diisopropylethylamine → 4-{4-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-4-oxo-butyl}-3-methyl-benzoic Acid Methyl Ester
Reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][O:26][C:27](=[O:41])[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][C:37]([OH:39])=O)=[C:30]([CH3:40])[CH:29]=1.Cl.[CH3:43][C:44]([CH3:54])([CH3:53])[CH2:45][CH2:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.CCN(C(C)C)C(C)C>ClCCl>[CH3:25][O:26][C:27](=[O:41])[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][C:37]([N:50]2[CH2:51][CH2:52][N:47]([CH2:46][CH2:45][C:44]([CH3:54])([CH3:53])[CH3:43])[CH2:48][CH2:49]2)=[O:39])=[C:30]([CH3:40])[CH:29]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
HBTU (910 mg, 2.4 mmol) was added to a solution of 4-(3-carboxy-propyl)-3-methyl-benzoic acid methyl ester from Example E30 (378 mg, 1.6 mmol) and 1-(3,3-dimethyl-butyl)-piperazine hydrochloride from Example E4 (467 mg, 1.9 mmol) in dichloromethane (15 ml) and DIEA (0.836 ml, 4.8 mmol). The mixture was stirred for 20 h at room temperature, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel through an isolute (eluant; 5% methanol:95% dichloromethane) to yield the title compound (582 mg, 94%).
Workup
- washwashed with saturated NaHCO3
- dry with materialbrine, dried
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography on silica gel through an isolute (eluant; 5% methanol:95% dichloromethane)
Sources & evidence
- ORD record
- ord-e93756c7ee574678828f7f2d375e5b91
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202858B2
Reaction notes
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