Ethylmorpholine → HCID 67709619, compound

HRID 1490091Notes

Reaction equation

HRID 1490091 reaction equation
C([N:3]1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1.[ClH:24].[C:25]([C:28]1[CH:38]=[CH:37][C:31]([CH:32]=[CH:33][C:34]([OH:36])=O)=[CH:30][CH:29]=1)(=[NH:27])N.Cl.[NH2:40][CH2:41][CH2:42][N:43]([CH2:61][C:62]([O:64][CH3:65])=[O:63])[C:44]([O:46][CH2:47][CH:48]1[C:60]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=2[C:54]2[C:49]1=[CH:50][CH:51]=[CH:52][CH:53]=2)=[O:45].OC1C2N=NNC=2C=CC=1>CN(C)C=O>[ClH:24].[NH2:3][N:27]=[CH:25][C:28]1[CH:29]=[CH:30][C:31]([CH:32]=[CH:33][C:34]([NH:40][CH2:41][CH2:42][N:43]([CH2:61][C:62]([O:64][CH3:65])=[O:63])[C:44]([O:46][CH2:47][CH:48]2[C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][C:54]=3[C:55]3[C:60]2=[CH:59][CH:58]=[CH:57][CH:56]=3)=[O:45])=[O:36])=[CH:37][CH:38]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 21480541HCID 21480541, compoundHCID 86751448HCID 86751448, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 67709619HCID 67709619, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

0.7 g (6 mmol) of N-ethylmorpholine and 0.8 g (4 mmol) of DCC are added, at 0° C., to 0.7 g (3 mmol) of 4-amidinocinnamic acid hydrochloride, 1.2 g (3 mmol) of methyl N-(2-aminoethyl)-N-(9-fluorenylmethoxycarbonyl)aminoacetate hydrochloride and 0.4 g (3 mmol) of hydroxybenzotriazole in 20 ml of dimethylformamide. The mixture is stirred at 0° C. for one hour and then at room temperature for 20 h, filtered from the precipitated urea and concentrated. The residue is taken up in ethyl acetate and washed with sodium hydrogen carbonate solution, and the organic phase is dried and concentrated. The product is chromatographed, for purification, on Sephadex LH20 using an homogeneous mixture of butanol/glacial acetic acid/water.

Workup

  1. waitat room temperature for 20 h
  2. filtrationfiltered from the precipitated urea
  3. concentrationconcentrated
  4. washwashed with sodium hydrogen carbonate solution
  5. customthe organic phase is dried
  6. concentrationconcentrated
  7. customThe product is chromatographed, for purification, on Sephadex
  8. additionan homogeneous mixture of butanol/glacial acetic acid/water

Sources & evidence

ORD record
ord-05f4016757ae4bd2a406ced910fa4874
Source dataset
uspto-grants-1997_10
Patent number
US05681838

Reaction notes

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