Dimethylamine → Genevant CL1

HRID 530161Notes

Reaction equation

CN(C)CC[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][CH3:21])=[O:9].[CH3:44][NH:45][CH3:46].[CH2:47](O)C>>[CH3:44][N:45]([CH3:47])[CH2:46][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][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:9]

Participants

Reactant 3

HCID 674Dimethylamine

HCID 702Ethanol

HCID 89775017(6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 6-(dimethylamino)hexanoate

Product 1

HCID 89775021Genevant CL1

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,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 5-(dimethylamino)pentanoate 13 was obtained as a pale yellow oil (1.9 g, 62%) from 5.6 M dimethylamine in ethanol (20 mL). 1H NMR (400 MHz, CDCl3) δ 5.45-5.28 (m, 6H), 4.95-4.90 (m, 1H), 2.34-2.23 (m, 4H), 2.23-2.20 (s, 6H), 2.06-1.92 (m, 12H), 1.70-1.58 (m, 5H), 1.58-1.44 (m, 5H), 1.44-1.15 (m, 25H), 0.92-0.87 (m, 9H). Rf 0.4 (10% MeOH—CH2Cl2).

Sources & evidence

ORD record: ord-b1a42422e30f40478b62c1d1b370fa34
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09352042B2

Reaction notes

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