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Diisopropylethylamine → (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-yl 4-(dimethylamino)butanoate

HRID 1259008
Notes
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Reaction equation

HRID 1259008 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]/[CH:51]=[CH:52]\[CH2:53]/[CH:54]=[CH:55]\[CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[CH:22]([OH:41])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Cl.[CH3:62][N:63]([CH3:70])[CH2:64][CH2:65][CH2:66][C:67](O)=[O:68].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>ClCCl.CN(C1C=CN=CC=1)C>[CH3:62][N:63]([CH3:70])[CH2:64][CH2:65][CH2:66][C:67]([O:41][CH:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:21]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]/[CH:51]=[CH:52]\[CH2:53]/[CH:54]=[CH:55]\[CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:68]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 126916404-(Dimethylamino)butyric acid hydrochlorideHCID 86667532(12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-ol

Product 1

HCID 86300806
(12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-yl 4-(dimethylamino)butanoate
Yield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-ol (450 mg, 0.54 mmol), 4-(dimethylamino)butanoic acid hydrochloride (135 mg, 0.8 mmol), EDCI hydrochloride (153 mg, 0.8 mmol), DIPEA (260 μL, 1.6 mmol) in anhydrous dichloromethane (10 mL) was added DMAP (5 mg). The solution was refluxed for 3 hours, cooled to room temperature and concentrated in vacuo to dryness. The reaction mixture was purified by column chromatography on silica gel 60 (eluted with a gradient of 100% hexanes to 1:1 hexanes/ethyl acetate) to afford (12Z,15Z)-1,2-bis((9Z,12Z)-octadeca-9,12-dienyloxy)henicosa-12,15-dien-3-yl 4-(dimethylamino)butanoate as a colorless oil (236 mg). 5.43-5.29 (m, 2H), 5.05-4.98 (m, 1H), 3.68-3.64 (m, 1H), 3.52-3.46 (m, 1H), 3.40 (t, 2H, J=6.7 Hz), 2.78 (t, 6H, J=6.4 Hz), 2.46-2.35 (m, 4H), 2.32 (s, 6H), 2.09-2.02 (m, 12H), 1.91-1.81 (m, 2H), 1.70-1.48 (m, 6H), 1.41-1.23 (m, 50H), 0.90 (t, 9H, J=6.7 Hz).

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. concentrationconcentrated in vacuo to dryness
  3. customThe reaction mixture was purified by column chromatography on silica gel 60 (
  4. washeluted with a gradient of 100% hexanes to 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-aafd1d402ec34b068edda9b461ad6077
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466122B2

Reaction notes

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