Triethylamine → HCID 86300946, compound

HRID 1259011Notes

Reaction equation

HRID 1259011 reaction equation
[C:1](Cl)(=[O:40])[O:2][CH:3]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[CH3:42][N:43]([CH3:66])[CH2:44][CH2:45][CH2:46][NH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]/[CH:56]=[CH:57]\[CH2:58]/[CH:59]=[CH:60]\[CH2:61][CH2:62][CH2:63][CH2:64][CH3:65].C(N(CC)CC)C>ClCCl>[CH3:66][N:43]([CH3:42])[CH2:44][CH2:45][CH2:46][N:47]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]/[CH:56]=[CH:57]\[CH2:58]/[CH:59]=[CH:60]\[CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[C:1](=[O:40])[O:2][CH:3]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86667533HCID 86667533, compoundHCID 86667534HCID 86667534, compound

Product 1

HCID 86300946HCID 86300946, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-yl carbonochloridate (590 mg, 1.0 mmol), N,N-dimethyl-N′-((9Z,12Z)-octadeca-9,12-dienyl)propane-1,3-diamine (350 mg, 1 mmol) and triethylamine (500 μL, 3.6 mmol) in dichloromethane (8 mL) was stirred overnight at room temperature. Upon completion, the solution was concentrated in vacuo to dryness and purified by column chromatography on silica gel to afford (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-yl 3-(dimethylamino)propyl((9Z,12Z)-octadeca-9,12-dienyl)carbamate as a colorless oil (500 mg, 55%). 1H NMR (CDCl3, 400 MHz) δ 5.42-5.28 (m, 12H), 4.79-4.70 (m, 1H), 3.32-3.12 (m, 4H), 2.78 (t, 6H, J=6.3 Hz), 2.38-2.20 (m, 8H), 2.09-2.02 (m, 12H), 1.82-1.63 (m, 2H), 1.57-1.43 (m, 6H), 1.41-1.23 (m, 52H), 0.89 (t, 9H, J=7.0 Hz).

Workup

  1. concentrationUpon completion, the solution was concentrated in vacuo to dryness
  2. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c8a6a27d589945c6b5430f16eefe73e9
Source dataset
uspto-grants-2013_06
Patent number
US08466122B2

Reaction notes

Loading…