Triethylamine → HCID 9812397, Verbindung

HRID 480541

Reaktionsgleichung

Reaktionsgleichung von HRID 480541
[O:1]=[C:2]1[O:7][C:6](=[O:8])[CH2:5][N:4]([CH2:9][CH2:10][N:11]([CH2:16][CH2:17][N:18]2[CH2:23][C:22](=[O:24])[O:21][C:20](=[O:25])[CH2:19]2)[CH2:12][C:13]([OH:15])=[O:14])[CH2:3]1.Cl.[NH2:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51].CC[N:55]([CH2:58][CH3:59])CC>CN(C=O)C>[C:13]([CH2:12][N:11]([CH2:10][CH2:9][N:4]([CH2:3][C:2]([OH:7])=[O:1])[CH2:5][C:6](=[O:8])[NH:55][CH2:58][CH2:59][O:30][CH2:31][CH2:32][O:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:16][CH2:17][N:18]([CH2:19][C:20]([NH:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[O:25])[CH2:23][C:22]([OH:21])=[O:24])([OH:15])=[O:14]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 100825DTPA dianhydrideHCID 85772808HCID 85772808, Verbindung

Produkt 1

HCID 9812397HCID 9812397, VerbindungAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N,N-Bis[2-(2,6-dioxo-4-morpholinyl)ethyl]glycine (1.9 g; 5.5 mmol) (commercial product) was added to a solution of octadecanoic acid 2-(2-aminoethoxy)ethyl ester hydrochloride (4.5 g; 11 mmol) and Et3N (1.5 g; 14 mmol) in DMF (150 mL) at 60° C. After 5 min the temperature was decreased to 45° C. After 2.5 h the mixture was cooled to room temperature to give a precipitate that was filtered, washed with acetone/H2O 15/5, then with acetone. The crude was dissolved in acetone and 0.1 N HCl and the solution heated at 50° C. After 10 min the solution was cooled to room temperature to afford a precipitate which was filtered, washed with acetone/H2O 15/5 then with acetone and dried under reduced pressure to give the desired compound (1.7 g; 1.5 mmol). Yield 27%. HPLC: 100% (area %). HPCE: 100% (area). K.F.: 3.11%. Weight loss (120° C.): 4.49%. The 1H-NMR, 13C-NMR, MS and IR spectra were consistent with the structure.

Aufarbeitung

  1. customto give a precipitate that
  2. filtrationwas filtered
  3. washwashed with acetone/H2O 15/5
  4. dissolutionThe crude was dissolved in acetone
  5. temperature0.1 N HCl and the solution heated at 50° C
  6. temperatureAfter 10 min the solution was cooled to room temperature
  7. customto afford a precipitate which
  8. filtrationwas filtered
  9. washwashed with acetone/H2O 15/5
  10. dry with materialwith acetone and dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b6848dee211143ea92c74016e72068a6
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06652834B2

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