4-Methylmorpholine → Benzyl (tert-butoxycarbonyl)glycylglycinate

HRID 1199233

Reaktionsgleichung

[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.CCN=C=NCCCN(C)C.[NH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].S(C1C=CC(C)=CC=1)([O-])(=O)=O.CN1CCOCC1>C(Cl)(Cl)Cl.C(#N)C>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([NH:24][CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: -15 °C

Versuchsvorschrift

Boc-Gly-OH (17.52 g, 0.1 mole) in a mixture of CHCl3 (50 ml) and acetonitrile (50 ml) was cooled to -15° C. and EDCI (19.17 g, 0.1 mole) was added and stirred for 20 minutes. To this, a pre-cooled solution of H-Gly-OBzl.tosylate (37.1 g, 0.11 mole), NMM (12.09 ml, 0.11 mole) in CHC13(100 ml) was added and stirred overnight at room temperature. After removing the solvent, the residue was taken in CHCl3 and extracted with acid and base. Chloroform was removed under reduced pressure, triturated with pet. obtain 30.2 g of I (yield: 93.7%), m.p. 82°-83° C. Rf2, 0.52; Rf4, 0.82. Anal. Cald. for C16H22N2O5 : C, 59.61; H, 6.88, N, 8.69%. Found: C, 59.43; H, 6.88; N, 8.35%.

Aufarbeitung

stirringstirred overnight at room temperature
customAfter removing the solvent
extractionextracted with acid and base
customChloroform was removed under reduced pressure
customtriturated with pet

Quellen und Nachweise

ORD-Eintrag: ord-89eb3fb264a844b8a12505c50a5d6284
Quelldatensatz: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04898926

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