1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 70291844, Verbindung

HRID 365428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 365428
C(OC(C[NH:9][C@H:10]([CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)[C:11]([OH:13])=O)=O)(C)(C)C.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[Cl:46][C:47]([Cl:74])([Cl:73])[CH2:48][O:49][C:50](=[O:72])[NH:51][CH2:52][CH2:53][CH2:54][CH2:55][C@@H:56]([C:69](=[O:71])[NH2:70])[NH:57][C:58](=[O:68])[C@H:59]([NH:66][CH3:67])[CH2:60][C:61]1[S:62][CH:63]=[CH:64][CH:65]=1>C(Cl)Cl>[Cl:74][C:47]([Cl:46])([Cl:73])[CH2:48][O:49][C:50](=[O:72])[NH:51][CH2:52][CH2:53][CH2:54][CH2:55][C@H:56]([NH:57][C:58](=[O:68])[C@H:59]([NH:66][CH2:67][C:11](=[O:13])[C@H:10]([NH2:9])[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)[CH2:60][C:61]1[S:62][CH:63]=[CH:64][CH:65]=1)[C:69](=[O:71])[NH2:70]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 54403579HCID 54403579, VerbindungHCID 54532855HCID 54532855, Verbindung

Produkt 1

HCID 70291844HCID 70291844, VerbindungAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(2R)-2-(tert-Butoxycarbonylmethylamino)-3-(2-napthyl)propionic acid (5.00 g; 15.8 mmole), HOAt (2.35 g; 17 mmole) and EDAC (3.03 g; 15.8 mmole) were added to methylene chloride (200 ml) and stirred for 15 min. [(5S)-5-carbamoyl-5-((2R)-2-methylamino-3-(2-thienyl)propionylamino)pentyl]carbamic acid 2,2,2-trichloroethyl ester (7.01 g; 14.5 mmole) was added and the mixture was stirred overnight. Methylene chloride (200 ml) was added and the organic phase was washed with water (200 ml), an aqueous solution of sodium hydrogensulphate (200 ml), an aqueous solution of sodium hydrogencarbonate (200 ml) and water (200 ml). The organic phase was dried (magnesium sulphate) and the solvent was removed in vacuo. The residue was dissolved in a mixture of trifluoroacetic acid (30 ml) and methylene chloride (70 ml) and stirred for 15 min. Water (150 ml) and sodium hydrogencarbonate were added to neutral pH, the phases were separated and the aqueous phase was extracted with methylene chloride (2×100 ml) and the phases were separated. The combined organic phase were dried (magnesium sulphate) and the solvent was removed in vacuo and the residue was chromatographed on silica using a mixture of aqueous ammonia in water (25%), ethanol and methylene chloride (0.7:9.3:90) as eluent to afford 6.3 g of ((5S)-5-{(2R)-2-[((2R)-2-amino-3-(2-naphthyl)propionyl)methylamino]-3-(2-thienyl)propionylamino}-5-carbamoylpentyl)carbamic acid 2,2,2-trichloroethyl ester.

Aufarbeitung

  1. additionwas added
  2. washthe organic phase was washed with water (200 ml)
  3. dry with materialThe organic phase was dried (magnesium sulphate)
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in a mixture of trifluoroacetic acid (30 ml) and methylene chloride (70 ml)
  6. stirringstirred for 15 min
  7. additionWater (150 ml) and sodium hydrogencarbonate were added to neutral pH
  8. customthe phases were separated
  9. extractionthe aqueous phase was extracted with methylene chloride (2×100 ml)
  10. customthe phases were separated
  11. dry with materialThe combined organic phase were dried (magnesium sulphate)
  12. customthe solvent was removed in vacuo
  13. customthe residue was chromatographed on silica using
  14. additiona mixture of aqueous ammonia in water (25%), ethanol and methylene chloride (0.7:9.3:90) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-d1f05fedca9e403e891204acdab8b305
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127341

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