Acetic Anhydride → 6,12,18-Tris(benzyloxy)-7,13,19-trioxo-6,12,18-triazaeicosanenitrile

HRID 1109847

Reaktionsgleichung

Reaktionsgleichung von HRID 1109847
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([O:15][N:16]([C:23](=[O:52])[CH2:24][CH2:25][CH2:26][CH2:27][N:28]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:29](=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1.C(Cl)Cl>[CH2:8]([O:15][N:16]([C:23](=[O:52])[CH2:24][CH2:25][CH2:26][CH2:27][N:28]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:29](=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][N:34]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:1](=[O:3])[CH3:2])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

5

Edukt 2

HCID 7918Acetic AnhydrideHCID 99862666,12,18-Tris(benzyloxy)-7,13-dioxo-6,12,18-triazaoctadecanenitrile

Produkt 1

HCID 101008386,12,18-Tris(benzyloxy)-7,13,19-trioxo-6,12,18-triazaeicosanenitrileAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Acetic anhydride (8 mL) was slowly added to a solution of (8) (1.25 g, 2.03 mmol) in pyridine (50 mL) and CH2Cl2 (30 mL) which had been cooled to 0° C. Stirring was continued at 0° C. for 30 minutes and then at room temperature overnight. Solvents were removed under high vacuum, and the residue was dissolved in CHCl3 (120 mL), followed by washing with 0.5N HCl (2×40 mL) and saturated NaHCO3 (2×40 mL). After solvent removal, the crude oil was purified by silica gel column chromatography, eluting with 3:1 EtOAc/hexane, to furnish 0.8 g (60%) of (9) as an oil: NMR δ 1.40-1.80 (m, 12 H), 2.05 (s, 3 H), 2.20-2.50 (m, 6 H), 3.40-3.73 (m, 6 H), 4.75 (s, 6 H) , 7.32 (s, 15 H). Anal. (C38H48N4O6) C, H, N.

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. customSolvents were removed under high vacuum
  4. dissolutionthe residue was dissolved in CHCl3 (120 mL)
  5. washby washing with 0.5N HCl (2×40 mL) and saturated NaHCO3 (2×40 mL)
  6. customAfter solvent removal
  7. customthe crude oil was purified by silica gel column chromatography
  8. washeluting with 3:1 EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-215dcef00ec74818b619f710d9eaf4cb
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05322961

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