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Triethylamine → {3-[1-[tert-Butoxycarbonyl-(2-methoxy-ethyl)-amino]-2-(tert-butyl-dimethyl-silanyloxy)ethyl]-phenyl}-carbamic acid benzyl ester

HRID 221408
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 221408
[CH2:1]([O:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([NH:27][CH2:28][CH2:29][O:30][CH3:31])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[O:40](C(OC(C)(C)C)=O)[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([N:27]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:40])[CH2:28][CH2:29][O:30][CH3:31])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 67329562{3-[2-(tert-Butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethylamino)-ethyl]-phenyl}-carbamic acid benzyl ester

Produkt 1

HCID 67329507{3-[1-[tert-Butoxycarbonyl-(2-methoxy-ethyl)-amino]-2-(tert-butyl-dimethyl-silanyloxy)ethyl]-phenyl}-carbamic acid benzyl esterAusbeute 32,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

{3-[2-(tert-Butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethylamino)-ethyl]-phenyl}-carbamic acid benzyl ester (1 g) was dissolved in dry DCM (10 mL) and stirred under argon at 0° C. Triethylamine (0.4 g) and (BOC)2O (0.52 g) were added and the reaction mixture was stirred at room temperature for 2 days. The reaction was quenched by addition of water and the mixture extracted with DCM. The organic phase was separated, dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography to give the title compound (400 mg).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 2 days
  2. customThe reaction was quenched by addition of water
  3. extractionthe mixture extracted with DCM
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give a crude product which
  8. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4ded7f318f4b4698985b135ca87c0d50
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08207167B2

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