Diethylamine → HCID 57500235, compound

HRID 537841Notes

Reaction equation

HRID 537841 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].CS(O[CH2:11][CH2:12][CH2:13][N:14]([C:16]([O:18][CH:19]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]/[CH:46]=[CH:47]\[CH2:48]/[CH:49]=[CH:50]\[CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:17])[CH3:15])(=O)=O>CCO.C(Cl)Cl>[CH2:1]([N:3]([CH2:4][CH3:5])[CH2:11][CH2:12][CH2:13][N:14]([CH3:15])[C:16](=[O:17])[O:18][CH:19]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]/[CH:46]=[CH:47]\[CH2:48]/[CH:49]=[CH:50]\[CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH3:2]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 86684847HCID 86684847, compound

Product 1

HCID 57500235HCID 57500235, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of diethylamine (2 mL) in EtOH (10 mL) was treated with 3-((((6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-yloxy)carbonyl)(methyl)amino)propyl methanesulfonate (500 mg, 0.7 mmol) in CH2Cl2 (2.5 mL). The solution was stirred (50 h), concentrated and subjected to chromatography (EtOAc) to yield (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-yl (3-(diethylamino)propyl)(methyl)carbamate (207 mg, 42%) as a pale yellow oil. Rf 0.43 (10% CH3OH—CH2Cl2), 1H NMR (400 MHz, CDCl3, δH) 5.41-5.28 (m, 8H, C═CH×8), 4.79-4.70 (m, 1H, CHO2CNR2), 3.28 (br. s, 2H, CH2NCH3), 2.94-2.83 (br. s, 3H, CO2NCH3), 2.79 (app. t, 4H, bis-allylic CH2×2), 2.52 (q, 4H, N(CH2CH3)2), 2.09-2.01 (m, 8H, CH2HC═C×4), 1.75-1.65 (m 4H, CH2×2), 1.59-1.45 (m, 4H, CH2×2), 1.42-1.22 (m, 36H, CH2×18), 1.15 (t, 6H, N(CH2CH3)2), 0.90 (t, 6H, CH3×2). FW 699.19, C46H86N2O2.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-4d990c957f7e40eaaaf941d615ab99ef
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

Loading…