N,N-Dimethyl-1,3-propanediamine → [11-(3-Dimethylaminopropylcarbamoyl)undecyl]carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:35][N:36]([CH3:41])[CH2:37][CH2:38][CH2:39][NH2:40]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:22])[NH:40][CH2:39][CH2:38][CH2:37][N:36]([CH3:41])[CH3:35])([CH3:2])([CH3:3])[CH3:4]Participants
Procedure
A mixture of 12-tert-butoxycarbonylaminododecanoic acid (3) (205 mg, 0.65 mmol) and 1,1′-Carbonyldiimidazole (114 mg, 0.70 mmol) in anhydrous THF (5 mL) was stirred at room temperature for 3 hours. 3-(Dimethylamino)propylamine (163 mL, 1.30 mmol) was then added via syringe and the reaction mixture stirred at room temperature for a further 24 hours. The solvent was then removed by rotary evaporation and the residue subjected to Biotage silica gel column chromatography (ethyl acetate/dichloromethane 5% to 75%, then methanol/dichloromethane 8%) to give the desired amide 4 (87.0 mg, 34%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.27 (m, 14H), 1.45 (s, 9H), 1.47 (m, 2H), 1.60 (m, 2H), 1.69 (m, 2H), 2.16 (t, 2H), 2.29 (s, 6H), 2.45 (t, 2H), 3.10 (m, 2H), 3.32 (m, 2H), 4.50 (br, 1H), 6.91 (br, 1H). m/z (ESI) 400 [C22H45N3O3+H]+.
Workup
- stirringthe reaction mixture stirred at room temperature for a further 24 hours
- customThe solvent was then removed by rotary evaporation
Sources & evidence
- ORD record
- ord-b8279d29b06c48dfb7ba3923ea3591c6
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07956059B2
Reaction notes
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