Trityl chloride → 2-(2-Hydroxyethyl)3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane

HRID 1614525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614525
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:30])[CH:6]([CH2:27][CH2:28][OH:29])[NH:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:31]1([C:37](Cl)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CN1CCOCC1>CN(C=O)C.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.CO>[OH:29][CH2:28][CH2:27][CH:6]([C:5](=[O:30])[NH:4][CH2:3][CH2:2][NH:1][C:37]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[NH:7][C:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 3

HCID 6456Trityl chlorideHCID 79724-MethylmorpholineHCID 194385476-Amino-2-(2-hydroxyethyl)-3-oxo-1-(triphenylmethyl)-1,4-diazahexane

Produkt 1

HCID 194385132-(2-Hydroxyethyl)3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptaneAusbeute 27,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 19609075Chloroform toluene methanolLösungsmittel

Versuchsvorschrift

6-Amino-2-(2-hydroxyethyl)-3-oxo-1-(triphenylmethyl)-1,4-diazahexane (15.0 g, 37.2 mmol) (Example 9 (a)) was dissolved in 150 ml DMF and triphenylmethyl chloride (10.35 g, 37.2 mmol) and methylmorpholine (3.75 g, 37.2 mmol) was added. After being stirred for 24 hours at ambient temperature, the reaction mixture was filtered and poured into 200 ml of ice water. After 1 hour stirring, filtration and thoroughly washing the precipitate with water, the solid was dried in vacuo at 50° C. to yield 22 g of crude product. The product was dissolved in chloroform/toluene/methanol (80/16/14) and purified on silica to yield 6.6 g (27%) of 2-(2-hydroxyethyl)3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane as white crystals, m.p. 71°-72° C., FAB MS: 646(M+1). The structure was confirmed by 13C NMR.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. additionpoured into 200 ml of ice water
  3. stirringAfter 1 hour stirring
  4. filtrationfiltration
  5. washthoroughly washing the precipitate with water
  6. customthe solid was dried in vacuo at 50° C.
  7. customto yield 22 g of crude product
  8. custompurified on silica

Quellen und Nachweise

ORD-Eintrag
ord-400c8067311e4aa5a463c07a88840ec3
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05198208

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