Diphosgene → (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 3-(dimethylamino)propyl(methyl)carbamate

HRID 530166

Reaktionsgleichung

Reaktionsgleichung von HRID 530166
[CH2:1]([CH:11]([CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:12]([OH:23])[CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].O=C(Cl)[O:36][C:37](Cl)(Cl)Cl.[CH3:42][N:43]([CH3:49])[CH2:44][CH2:45][CH2:46][NH:47][CH3:48]>C(OCC)C>[CH3:42][N:43]([CH3:49])[CH2:44][CH2:45][CH2:46][N:47]([CH3:48])[C:37](=[O:36])[O:23][CH:12]([CH:11]([CH2:1][CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

5

Edukt 3

HCID 10426DiphosgeneHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 89775018(6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-ol

Produkt 1

HCID 89775024(6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 3-(dimethylamino)propyl(methyl)carbamateAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

A solution of (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-ol 8 (0.5 g, 1.1 mmol) in anhydrous diethyl ether (10 mL) was added slowly a solution of diphosgene (0.2 mL, 1.8 mmol) in anhydrous diethyl ether cooled to approximately −15° C. The solution was stirred for 1 hour then N,N,N′-trimethyl-1,3-propanediamine (1.3 mL, 8.7 mmol) was added at −15° C. The solution was warmed to room temperature, stirred for 1 hour, and then filtered to remove the ammonium salts and urea. The diethyl ether filtrate was concentrated in vacuo to dryness. The residue was purified by column chromatography (100% ethyl acetate) to afford (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-yl 3-(dimethylamino)propyl(methyl)carbamate 23 as a colorless oil (0.15 g, 23%), 1H NMR (400 MHz, CDCl3) δ 5.41-5.29 (m, 6H), 4.85-4.77 (m, 1H), 3.35-3.21 (m, 2H), 2.93-2.81 (m, 3H), 2.31-2.17 (m, 8H), 2.08-1.92 (m, 12H), 1.75-1.64 (m, 2H), 1.64-1.15 (m, 31H), 0.92-0.85 (m, 9H). Rf 0.45 (10% MeOH—CH2Cl2).

Aufarbeitung

  1. temperatureThe solution was warmed to room temperature
  2. stirringstirred for 1 hour
  3. filtrationfiltered
  4. customto remove the ammonium salts and urea
  5. concentrationThe diethyl ether filtrate was concentrated in vacuo to dryness
  6. customThe residue was purified by column chromatography (100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-758afab1823f4443b99a1a546d9317cf
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09352042B2

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