N-Methylethylamine → HCID 86684846, compound

HRID 537840Notes

Reaction equation

HRID 537840 reaction equation
[CH2:1]([NH:3][CH3:4])[CH3:2].CS(O[CH2:10][CH2:11][CH2:12][N:13]([C:15]([O:17][CH:18]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]/[CH:45]=[CH:46]\[CH2:47]/[CH:48]=[CH:49]\[CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:16])[CH3:14])(=O)=O>CCO.C(Cl)Cl>[CH2:1]([N:3]([CH3:4])[CH2:10][CH2:11][CH2:12][N:13]([CH3:14])[C:15](=[O:16])[O:17][CH:18]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]/[CH:45]=[CH:46]\[CH2:47]/[CH:48]=[CH:49]\[CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH3:2]

Participants

5

Reactant 2

HCID 12219N-MethylethylamineHCID 86684847HCID 86684847, compound

Product 1

HCID 86684846HCID 86684846, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethylmethylamine (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-(ethyl(methyl)amino)propyl)(methyl)carbamate (305 mg, 64%) as a pale yellow oil. Rf 0.41 (10% CH3OH—CH2Cl2), 1H NMR (400 MHz, CDCl3, δH) 5.47-5.34 (m, 8H, C═CH×8), 4.81-4.75 (m, 1H, CHO2CNR2), 3.33 (br. s, 2H, CH2NCH3), 2.94 (br. s, 3H, CO2NCH3), 2.83 (app. t, 4H), 2.45 (q, 2H, N(CH3)CH2CH3), 2.37 (t, 2H, CH2N(CH3)CH2CH3), 2.25 (s, 3H, N(CH3)CH2CH3), 2.14-2.07 (m, 8H, CH2HC═C×4), 1.81-1.70 (m, 4H, CH2×2), 1.62-1.50 (m, 4H, CH2×2), 1.46-1.25 (m, 34H, CH2×17), 1.09 (t, 3H, CH3NCH2CH3), 0.93 (t, 6H, H3×2), FW 685.16, C45H84N2O2.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-54d4a156443640638ef8dcac2cb799d9
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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