Dimethylamine → (6Z,15Z)-11-((Z)-dec-4-enyl)henicosa-6,15-dien-10-yl 6-(dimethylamino)hexanoate
Reaction equation
[CH3:1][N:2]([CH3:43])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH:11]([CH:22]([CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20]C)=[O:9].CNC>C(O)C>[CH3:43][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH:11]([CH:22]([CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:9]Participants
4
Procedure
Using an analogous procedure to that described for the synthesis of (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 6-(dimethylamino)hexanoate 11, (6Z,15Z)-11-((Z)-dec-4-enyl)henicosa-6,15-dien-10-yl 6-(dimethylamino)hexanoate 21 was obtained as a colorless oil (1.2 g, 92%) from 5.6 M dimethylamine in ethanol (15 mL). 1H NMR (400 MHz, CDCl3) δ 5.44-5.28 (m, 6H), 4.95-4.88 (m, 1H), 2.33-2.19 (m, 10H), 2.08-1.90 (m, 12H), 1.70-1.23 (m, 9H), 1.23-1.14 (m, 26H), 0.93-0.85 (m, 9H). Rf 0.15 (10% MeOH—CH2Cl2).
Sources & evidence
- ORD record
- ord-aecd5ad04d5d46219a04c4c29b2b0def
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09352042B2
Reaction notes
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