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

HRID 1733795Notes

Reaction equation

HRID 1733795 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 194385132-(2-Hydroxyethyl)3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptaneYield 27.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 19609075Chloroform toluene methanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7b9d8204cc484affba55ed0b1fdcaa8f
Source dataset
uspto-grants-1996_07
Patent number
US05531978

Reaction notes

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