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Triethylamine → N-(4-nitrobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamide

HRID 987041
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 987041
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][CH:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[N+:28]([C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1)([O-:30])=[O:29].C(N(CC)CC)C>C1COCC1.CN(C=O)C>[N+:28]([C:31]1[CH:32]=[CH:33][C:34]([CH2:35][NH:36][C:13]([CH:9]2[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:12][CH2:11][S:10]2)=[O:15])=[CH:37][CH:38]=1)([O-:30])=[O:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 291474-NitrobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 46440943-(tert-Butoxycarbonyl)-1,3-thiazolidine-2-carboxylic acid

Produkt 1

HCID 21918695N-(4-nitrobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3-(t-butoxycarbonyl)thiazolidine-2-carboxylic acid (1 g, 4.3 mmol) and carbonyldiimidazole (0.7 g, 4.3 mmol) are dissolved in THF (10 ml). the mixture is agitated for 1 hour at ambient temperature. 4-nitrobenzylamine (0.81 g, 4.3 mmoles) and triethylamine (0.6 ml. 0.43 g, 4.3 mmoles) in suspension in 10 ml of a THF and DMF mixture (1/1) are added to the preceding solution and the whole is heated under reflux for 5 hours. The solvents are then evaporated off under reduced pressure. The residue is taken up in 25 ml of ethyl acetate and washed 3 times with 15 ml of water. The organic phase is dried and the solvent is evaporated off under reduced pressure. The product obtained is purified on silica gel in a dichloromethane/methanol mixture (95/5). N-(4-nitrobenzyl)-3-(t-butoxycarbonyl)thiazolidine-2-carboxamide is obtained in the form of a pale yellow oil with a yield of 80% (1.25 g).

Aufarbeitung

  1. temperaturethe whole is heated
  2. temperatureunder reflux for 5 hours
  3. customThe solvents are then evaporated off under reduced pressure
  4. washwashed 3 times with 15 ml of water
  5. customThe organic phase is dried
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe product obtained
  8. customis purified on silica gel in a dichloromethane/methanol mixture (95/5)

Quellen und Nachweise

ORD-Eintrag
ord-84801aee34014f70ac9484def1a8ad64
Quelldatensatz
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06630461B2

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