Triethylamine → 1-[[[(4-isothiocyanatophenyl)carbonyl]amino]butyl]-N,N-diethyl-D-lysergamide

HRID 1108001

Reaktionsgleichung

Reaktionsgleichung von HRID 1108001
NC(C)[CH2:3][CH2:4][N:5]1[C:26]2[C:27]3[C:7]([CH2:8][C@@H:9]4[C:21]([C:22]=3[CH:23]=[CH:24][CH:25]=2)=[CH:20][C@@H:12]([C:13](=[O:19])[N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH2:11][N:10]4[CH3:28])=[CH:6]1.[N:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)=[C:31]=[S:32].[CH2:42]([N:44](CC)CC)[CH3:43]>C1COCC1>[N:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:44][CH2:42][CH2:43][CH2:3][CH2:4][N:5]2[C:26]3[C:27]4[C:7]([CH2:8][C@@H:9]5[C:21]([C:22]=4[CH:23]=[CH:24][CH:25]=3)=[CH:20][C@@H:12]([C:13](=[O:19])[N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH2:11][N:10]5[CH3:28])=[CH:6]2)=[O:38])=[CH:35][CH:34]=1)=[C:31]=[S:32]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 6376544-Isothiocyanatobenzoyl chlorideHCID 228945521-(3-aminobutyl)-N,N-diethyl-D-lysergamide

Produkt 1

HCID 228945541-[[[(4-isothiocyanatophenyl)carbonyl]amino]butyl]-N,N-diethyl-D-lysergamideAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 370 mg (0.94 mmol) of 5 in 15 mL of dry THF was cooled to 0° C. and treated with a solution of 190 mg (0.96 mmol) of 6 in 5 mL of dry THF, stirred at 0° C. for 30 minutes and then at room temperature overnight. The reaction mixture was treated with 0.14 mL (1.0 mmol) of triethylamine and stirred at room temperature for 2 hours The reaction mixture was concentrated at reduced pressure. The residue was dissolved in methylene chloride, washed with H2O, dried over anhydrous sodium sulfate and concentrated at reduced pressure. The residue was chromatographed on 200 g of silica gel using 3% methanol in methylene chloride as eluent to yield 325 mg (62%) of 7 as a tan amorphous solid [α]D =+47.5° (c=0.91%; CHCl3).

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. stirringstirred at room temperature for 2 hours The reaction mixture
  4. concentrationwas concentrated at reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washwashed with H2O
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was chromatographed on 200 g of silica gel using 3% methanol in methylene chloride as eluent

Quellen und Nachweise

ORD-Eintrag
ord-8a45b5c874d444979f4cb3e09adc6b78
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06063908

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