Triethylamine → Ethyl 4-{1-[(adamantan-1-ylcarbonyl)amino]-2-methylpropyl}benzoate
Reaction equation
[C:1]12([C:11]([OH:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:45][CH:46]([C:50]1[CH:60]=[CH:59][C:53]([C:54]([O:56][CH2:57][CH3:58])=[O:55])=[CH:52][CH:51]=1)[CH:47]([CH3:49])[CH3:48]>CN(C=O)C>[C:1]12([C:11]([NH:45][CH:46]([C:50]3[CH:60]=[CH:59][C:53]([C:54]([O:56][CH2:57][CH3:58])=[O:55])=[CH:52][CH:51]=3)[CH:47]([CH3:48])[CH3:49])=[O:13])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a vial charged with 1-adamantylcarboxylic acid (0.031 g, 0.17 mmol) was added HATU (64.6 mg, 0.17 mmol), triethylamine (0.14 mL, 1.02 mmol) and DMF (1 mL). The solution was shaken at rt for 1 h then ethyl 4-(1-amino-2-methylpropyl)benzoate (0.038 g, 0.17 mmol) in DMF (1 mL) was added. The resulting mixture was shaken at rt for 16 h. Solvent was then evaporated. To the residue was added DCE (3 mL) and sat. NaHCO3 solution (1.5 mL). After separation, the aqueous layer was extracted with DCE twice. Combined organic layers were concentrated to give crude ethyl 4-{1-[(adamantan-1-ylcarbonyl)amino]-2-methylpropyl}benzoate as a solid.
Workup
- stirringThe resulting mixture was shaken at rt for 16 h
- customSolvent was then evaporated
- additionTo the residue was added DCE (3 mL) and sat. NaHCO3 solution (1.5 mL)
- customAfter separation
- extractionthe aqueous layer was extracted with DCE twice
- concentrationCombined organic layers were concentrated
Sources & evidence
- ORD record
- ord-2645a3bf51694e8abbe29dba18e9ee51
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382197B2
Reaction notes
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