Water → HCID 57637077, Verbindung

HRID 1804570

Reaktionsgleichung

Reaktionsgleichung von HRID 1804570
[OH:1][NH:2][C:3]([CH:5]1[CH2:7][CH2:6]1)=[NH:4].[H-].[Na+].[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][C:20](OCC)=O)=[O:16])([CH3:13])([CH3:12])[CH3:11].O>CN(C)C=O>[CH:5]1([C:3]2[N:4]=[C:20]([CH2:19][CH2:18][NH:17][C:15](=[O:16])[O:14][C:10]([CH3:13])([CH3:12])[CH3:11])[O:1][N:2]=2)[CH2:7][CH2:6]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15933116Ethyl 3-{[(tert-butoxy)carbonyl]amino}propanoateHCID 178513214HCID 178513214, Verbindung

Produkt 1

HCID 57637077HCID 57637077, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

3.10 g (30.96 mmol) N-hydroxy-cyclopropanecarboxamidine are placed in 10 ml dimethylformamide and molecular sieve. 1.32 g (34.06 mmol) sodium hydride (60% in mineral oil) are added. The mixture is stirred for 0.1 hours at 50° C., then 7.40 g (34.06 mmol) ethyl 3-tert-butoxycarbonylamino-propionate in 20 ml dimethylformamide are added. The reaction mixture is stirred for 3 hours at 50° C. After cooling 15 ml of water are added, the mixture is suction filtered through Celite. The 2 phases of the filtrate are separated, the aqueous phase is extracted with ethyl acetate, the combined organic phase is evaporated down. The residue is purified by chromatography.

Aufarbeitung

  1. stirringThe reaction mixture is stirred for 3 hours at 50° C
  2. additionare added
  3. filtrationfiltered through Celite
  4. customThe 2 phases of the filtrate are separated
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. customthe combined organic phase is evaporated down
  7. customThe residue is purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b92374e1d935469980493c5a20a805db
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354418B2

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