Trityl chloride → N-(Triphenylmethyl)glycylglycine

HRID 251514

Reaktionsgleichung

Reaktionsgleichung von HRID 251514
[CH2:1]([NH2:9])[C:2]([NH:4][CH2:5][C:6]([OH:8])=[O:7])=[O:3].C(NCC)C.[C:15](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.CC(O)C>[NH:9]([C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:1][C:2]([NH:4][CH2:5][C:6]([OH:8])=[O:7])=[O:3]

Komponenten

6

Edukt 3

HCID 6456Trityl chlorideHCID 8021DiethylamineHCID 11163Glycylglycine

Produkt 1

HCID 14217166N-(Triphenylmethyl)glycylglycineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

6.6 g (50 mmol) of Gly-Gly (manufactured and sold by PEPTIDE INSTITUTE INC., Japan) was dissolved in a mixed solvent comprised of 20 ml of H2O, 40 ml of 2-propanol and 15 ml of diethylamine to obtain a solution. To the obtained solution was gradually added 18.1 g (65 mmol) of trityl chloride, followed by stirring for 1 hour. To the resultant reaction mixture was added H2O, to thereby generate a precipitate. The generated precipitate was recovered, washed with water and, then, dissolved in 5 ml of acetic acid, to thereby obtain an acidic solution. The solvents were distilled off from the obtained acidic solution under reduced pressure, to thereby obtain 13.1 g of Trt-Gly-Gly (192).

Aufarbeitung

  1. customto obtain a solution
  2. customTo the resultant reaction mixture
  3. customThe generated precipitate was recovered
  4. washwashed with water
  5. dissolutiondissolved in 5 ml of acetic acid
  6. customto thereby obtain an acidic solution
  7. distillationThe solvents were distilled off from the obtained acidic solution under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fa639492999b4528a1dd7f6272fed8cf
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863408B2

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