1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Boc-Phe-Phe-OEt

HRID 443730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 443730
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:20][C@H:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.CCN=C=NCCCN(C)C>C(Cl)(Cl)Cl>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH:20][C@H:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 165085Ethyl L-phenylalaninate hydrochloride

Produkt 1

HCID 12879039Boc-Phe-Phe-OEtAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In 150 ml of chloroform were dissolved 26.5 g of Boc-Phe-OH and 22.9 g of H-Phe-OEt.HCl, to which 18.4 ml of WSC was added under cooling at 0° C. This was then subjected to stirring for 2 hours at -10° C., then 15 hours at room temperature. The reaction solution was concentrated in vacuo and the residue was dissolved in 20 ml of ethyl acetate, washed successively with 1 N HCl, water, 5% aqueous NaHCO3 solution and water, dried over Na2SO4 then again concentrated in vacuo. The thus obtained residue was added to n-hexane and the resultant amorphous precipitate was collected, and was recrystallized from n-hexane, which gave 37 g (yield=84%) of the title product. m.p. 106.5°-107.5° C. [α]D25 -9.7° (C 1.3, DMF). Analysis--Calculated for C25H32O5N2 : C, 68.16; H, 7.32; N, 6.36. Found: C, 67.85; H, 7.32; N, 6.49.

Aufarbeitung

  1. custom15 hours
  2. customat room temperature
  3. concentrationThe reaction solution was concentrated in vacuo
  4. dissolutionthe residue was dissolved in 20 ml of ethyl acetate
  5. washwashed successively with 1 N HCl, water, 5% aqueous NaHCO3 solution and water
  6. dry with materialdried over Na2SO4
  7. concentrationthen again concentrated in vacuo
  8. additionThe thus obtained residue was added to n-hexane
  9. customthe resultant amorphous precipitate was collected
  10. customwas recrystallized from n-hexane, which

Quellen und Nachweise

ORD-Eintrag
ord-24278a5661844520b7ffd5a29dea2c06
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04261885

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