N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → Tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate

HRID 915016

Reaktionsgleichung

Reaktionsgleichung von HRID 915016
Cl.[NH2:2][CH:3]([C:12]1[CH:13]=[CH:14][C:15](=[O:21])[N:16]([CH:18]([CH3:20])[CH3:19])[N:17]=1)[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O=C1CCC(=O)N1[O:29][C:30](=O)[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH:18]([N:16]1[C:15](=[O:21])[CH:14]=[CH:13][C:12]([CH:3]([NH:2][C:30](=[O:29])[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[C:4](=[O:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[N:17]1)([CH3:19])[CH3:20]

Komponenten

5

Edukt 3

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 81531DiisopropylethylamineHCID 69331476HCID 69331476, Verbindung

Produkt 1

HCID 86600908Tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamateAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

Under ice-cooling, to a suspension of 6-(1-amino-2-oxo-2-phenylethyl)-2-isopropyl-3(2H)-pyridazinone hydrochloride (1.00 g) and tert-butyl {2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl}carbamate (973 mg) in CH2Cl2 (10 ml) was added ethyl(diisopropyl)amine (0.651 ml) and stirred at the same temperature for 2 hours and at 20-25° C. for 18 hours. The mixture was washed with water, dried over MgSO4 and concentrated under reduced pressure to give syrup. The syrup was purified by column chromatography on silica gel (EtOAc only) to give tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate as an amorphous solid (1.13 g).

Aufarbeitung

  1. washThe mixture was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customto give syrup
  5. customThe syrup was purified by column chromatography on silica gel (EtOAc only)

Quellen und Nachweise

ORD-Eintrag
ord-24b84654b7be4e2794f1aad9976c8871
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265120B2

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