Diisopropylethylamine → {[2-(Tert-butoxycarbonylamino)-ethyl]-methyl-amino}-acetic acid benzyl ester

HRID 604328

Reaktionsgleichung

Reaktionsgleichung von HRID 604328
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:24])[CH2:21][NH:22][CH3:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:25]([O:29][C:30]([NH:32][CH2:33][CH2:34]Br)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:12]([O:19][C:20](=[O:24])[CH2:21][N:22]([CH2:34][CH2:33][NH:32][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH3:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 122108994-Methylbenzene-1-sulfonic acid--benzyl N-methylglycinate (1/1)

Produkt 1

HCID 59650730{[2-(Tert-butoxycarbonylamino)-ethyl]-methyl-amino}-acetic acid benzyl esterAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

500 mg (1.42 mmol) of sarcosine benzyl ester p-toluenesulfonate, 478 mg (2.13 mmol) of 2-(tert-butoxycarbonylamino)-ethyl bromide, and 0.25 mL (2.13 mmol) of diisopropyl-ethylamine were dissolved in methylene chloride (10 mL), and then stirred at room temperature for approximately three days. After completion of the reaction, the reaction solution was concentrated and the residue obtained was purified by silica gel column chromatography (ethyl acetate) to yield 175 mg (38%) of {[2-(tert-butoxycarbonylamino)-ethyl]-methyl-amino}-acetic acid benzyl ester as a colorless viscous oil.

Aufarbeitung

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated
  3. customthe residue obtained
  4. customwas purified by silica gel column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d740dd80941b4c5092ccb95169bfac92
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910593B2

Verknüpfte Notizen

Wird geladen…