4-Methylmorpholine → Ethyl 3-(2-{(tert-butoxycarbonyl)amino}acetylamino)propionate

HRID 720934

Reaktionsgleichung

Reaktionsgleichung von HRID 720934
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH2:8])[CH3:3].[C:10]([O:14][C:15]([NH:17][CH2:18][C:19](O)=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].C1CCC(N=C=NC2CCCCC2)CC1.CN1CCOCC1>ClCCl>[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]([NH:8][CH2:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:9])=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 458475beta-Alanine, ethyl ester, hydrochloride

Produkt 1

HCID 21893946Ethyl 3-(2-{(tert-butoxycarbonyl)amino}acetylamino)propionateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of β-alanine ethyl ester hydrochloride salt (5) (3.07 g; 0.02 mmol), N-(tertbutoxycarbonyl)glycine (3.5 g; 0.02 mmol), DCCI (4.12 g; 0.02 mmol) and 4-methylmorpholine (2.2 ml) in dichloromethane (60 ml) was stirred overnight under argon atmosphere at ambient temperature. After filtration the residue was purified by flash chromatography eluting with dichloromethane/ethanol (96/4) to give ethyl 3-[(2-tertbutoxycarbonylaminoacetyl)amino]propanoate (6).

Aufarbeitung

  1. filtrationAfter filtration the residue
  2. customwas purified by flash chromatography
  3. washeluting with dichloromethane/ethanol (96/4)

Quellen und Nachweise

ORD-Eintrag
ord-a2f12b02ca7c40afb4b1912884e48d63
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135502B1

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