Diisopropylethylamine → tert-butyl(1-(2-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonyl)cyclopropyl)methylcarbamate

HRID 1427653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427653
CCN(C(C)C)C(C)C.[NH:10]([C:12]([C:14]1([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:16][CH2:15]1)=[O:13])[NH2:11].[CH2:26]([O:33][N:34]1[C:40](=[O:41])[N:39]2[CH2:42][C@H:35]1[CH2:36][CH2:37][CH:38]2[C:43](O)=[O:44])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:21]([O:20][C:19](=[O:25])[NH:18][CH2:17][C:14]1([C:12]([NH:10][NH:11][C:43]([CH:38]2[CH2:37][CH2:36][C@@H:35]3[CH2:42][N:39]2[C:40](=[O:41])[N:34]3[O:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:44])=[O:13])[CH2:16][CH2:15]1)([CH3:22])([CH3:24])[CH3:23]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66870453(5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acidHCID 89834475Tert-butyl(1-(hydrazinecarbonyl)cyclopropyl)methylcarbamate

Produkt 1

HCID 131732351tert-butyl(1-(2-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonyl)cyclopropyl)methylcarbamateAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

DIPEA (14 g, 0.11 mol) was added to a solution of tert-butyl (1-(hydrazinecarbonyl)cyclopropyl)methylcarbamate (10.0 g, 0.044 mol), (5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (10 g, 0.036 mol), and HATU (15 g, 0.04 mol) in CH2Cl2 (250 mL). The mixture was stirred at rt for 2 hrs. The mixture was diluted with CH2Cl2 (500 mL), washed with H2O (300 mL), dried over Na2SO4, and concentrated. The crude product was washed with EtOAc (200 mL), and filtrated to afford tert-butyl(1-(2-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarbonyl)cyclopropyl)methylcarbamate (15 g, 85%) as a white solid. ESI-MS (EI+, m/z): 488.3 [M+H]+.

Aufarbeitung

  1. washwashed with H2O (300 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. washThe crude product was washed with EtOAc (200 mL)
  5. filtrationfiltrated

Quellen und Nachweise

ORD-Eintrag
ord-d2418f84409f48bb8ea6336286a28c63
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933233B2

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