Dicyclohexylcarbodiimide → HCID 86751449, compound

HRID 1490092Notes

Reaction equation

HRID 1490092 reaction equation
[Na+].C(OC(N[C:10]([C:12]1[CH:22]=[CH:21][C:15]([CH:16]=[CH:17][C:18]([O-:20])=O)=[CH:14][CH:13]=1)=[NH:11])=O)(C)(C)C.C1CCC([N:29]=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[ClH:48].[NH2:49][CH2:50][CH2:51][N:52]1[CH2:56][C:55](=[O:57])[N:54]([CH:58]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:59]([O:61][CH3:62])=[O:60])[C:53]1=[O:69]>CN(C)C=O>[ClH:48].[NH2:29][N:11]=[CH:10][C:12]1[CH:13]=[CH:14][C:15]([CH:16]=[CH:17][C:18]([NH:49][CH2:50][CH2:51][N:52]2[CH2:56][C:55](=[O:57])[N:54]([CH:58]([C:63]3[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=3)[C:59]([O:61][CH3:62])=[O:60])[C:53]2=[O:69])=[O:20])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 86751451HCID 86751451, compoundHCID 161569249HCID 161569249, compound

Product 1

HCID 86751449HCID 86751449, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

730 mg (2.34 mmol) of 4-tert-butoxycarbonylamidinocinnamic acid sodium salt are dissolved in 50 ml of dimethylformamide and 531 mg (2.57 mmol) of DCC and 316 mg (2.34 mmol) of HOBt are then added at 0° C. The mixture is stirred for 50 minutes and 355 mg (2.34 mmol) of methyl (3-(2-aminoethyl)-2,5-dioxoimidazolidin-1-yl)phenylacetate hydrochloride are then added. After stirring at room temperature for 20 h, the mixture is concentrated and the residue is chromatographed, for purification, on silica gel using a mixture of methylene chloride, methanol, glacial acetic acid and water=85:15:2:2. The fractions containing the pure substance are concentrated and freeze dried.

Workup

  1. stirringAfter stirring at room temperature for 20 h
  2. concentrationthe mixture is concentrated
  3. customthe residue is chromatographed, for purification, on silica gel using
  4. additiona mixture of methylene chloride, methanol, glacial acetic acid and water=85:15:2:2
  5. additionThe fractions containing the pure substance
  6. concentrationare concentrated
  7. customfreeze dried

Sources & evidence

ORD record
ord-642066994e00408c8fc47688a7e9853b
Source dataset
uspto-grants-1997_10
Patent number
US05681838

Reaction notes

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