Triethylamine → HCID 86746783, Verbindung

HRID 247828

Reaktionsgleichung

Reaktionsgleichung von HRID 247828
[P:1](Cl)(Cl)([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:2].C(N(CC)CC)C.[CH2:19]([OH:28])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH3:29][CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[C:33]=1[NH:41][C:42](=[O:52])[CH2:43][NH:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH3:31]>C1(C)C=CC=CC=1>[CH3:31][CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:39])[CH3:40])[C:33]=1[NH:41][C:42](=[O:52])[CH2:43][N:44]([CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[P:1](=[O:2])([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[O:28][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:29]

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 89141-NonanolHCID 13038Phosphorodichloridic acid, phenyl esterHCID 19764427HCID 19764427, Verbindung

Produkt 1

HCID 86746783HCID 86746783, VerbindungAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To an ice-cooled solution of phenyl dichlorophosphate (2.83 g, 0.02 mol) in dry toluene (50 mL) is added triethylamine (2.02 g, 0.02 mol) followed by nonyl alcohol (2.89 g, 0.02 mol) in dry toluene (40 mL) dropwise. The reaction mixture is stirred in an ice bath for 2 hours and then filtered. To this filtrate are added triethylamine (2.02 g, 0.02 mol) and a solution of N-[2,6-bis(1-methylethyl)phenyl]-2-[phenylmethyl]amino-acetamide (Example V) (6.40 g, 0.02 mole) and the mixture is stirred at room temperature overnight. The reaction mixture is filtered and concentrated. Flash column chromatography and crystallization from ethyl acetate affords 3.8 g of the title compound; IR (KBr); 3285, 2961, 2925, 2858, 2367, 1684, and 1508. 1H NMR (250 MHz, DMSO)δ9.22 (1 H, s), 7.44-6.92 (13 H, m), 4.50-4.30 (2 H, m), 4.30-4.00 (2 H, m), 4.00-3.60 (2 H, m), 3.10-2.80 (2 H, m), 1.70-1.40 (2 H, m), 1.4-1.18 (12 H, m), 1.18-1.00 (12 H, d, J=7 Hz), 0.98-0.76 (3 H, m).

Aufarbeitung

  1. filtrationfiltered
  2. filtrationThe reaction mixture is filtered
  3. concentrationconcentrated
  4. customFlash column chromatography and crystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4686ccefd43947c99c2937b26ae79b6f
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208224

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