Triethylamine → HCID 24804103, compound
Reaction equation
[CH3:1][CH:2]([CH3:8])[CH2:3][CH2:4][C:5]([OH:7])=O.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.Cl.[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]1[N:38]=[C:37]([CH:39]2[CH2:44][CH2:43][NH2+:42][CH2:41][CH2:40]2)[O:36][N:35]=1>ClCCl>[CH3:8][CH:2]([CH3:1])[CH2:3][CH2:4][C:5]([N:42]1[CH2:43][CH2:44][CH:39]([C:37]2[O:36][N:35]=[C:34]([C:30]3[S:29][CH:33]=[CH:32][CH:31]=3)[N:38]=2)[CH2:40][CH2:41]1)=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
86 mg (2 eq.) of 4-methylvaleric acid, 141 mg (2 eq.) of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (EDCI) and 207 μl (4 eq.) of triethylamine were dissolved in 2 ml of dichloromethane. 100 mg (1 eq.) of 4-(3-thiophen-2-yl[1,2,4]oxadiazol-5-yl)piperidinium hydrochloride were then added to the reaction medium, which was then stirred at room temperature for 24 hours. The reaction medium was evaporated under reduced pressure and the residue was taken up in 20 ml of ethyl acetate. The organic phase was washed with aqueous 1N sodium hydroxide solution (3×30 ml), with aqueous 1N hydrochloric acid solution (3×30 ml) and with saturated aqueous NaCl solution (30 ml) and then dried over MgSO4 and concentrated under reduced pressure to give 102 mg (83%) of the expected compound.
Workup
- customThe reaction medium was evaporated under reduced pressure
- washThe organic phase was washed with aqueous 1N sodium hydroxide solution (3×30 ml), with aqueous 1N hydrochloric acid solution (3×30 ml) and with saturated aqueous NaCl solution (30 ml)
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-55522eaa7331470bba340519c90f29a3
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338599B2
Reaction notes
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