Triethylamine → HCID 86657585, Verbindung

HRID 1040426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040426
[C:1](NC1(C(O)=O)CC1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.CN(C(ON1[N:39]=[N:38][C:33]2[CH:34]=C[CH:36]=[N:37][C:32]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:47]([O:51][C:52](NN)=[O:53])([CH3:50])([CH3:49])[CH3:48].CC1C([O:63]C(C)=O)=CC(C(C)C)=C(OCC[NH+](C)C)C=1.[Cl-]>CN(C=O)C.O>[C:47]([O:51][C:52]([NH:39][NH:38][C:33]1([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:34][CH:32]1[N:37]=[C:36]=[O:63])=[O:53])([CH3:50])([CH3:49])[CH3:48]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 13758ArliteneHCID 70091tert-Butyl carbazateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15686068HCID 15686068, Verbindung

Produkt 1

HCID 86657585HCID 86657585, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-benzoylamino-cyclopropanecarboxylic acid (5.0 g, 21.3 mmol) in DMF (5 mL) was added Et3N (2.94 mL, 21.3 mmol) and HATU (8.08 g, 21.3 mmol). The reaction mixture was allowed to stir for 10 min then hydrazinecarboxylic acid tert-butyl ester (2.81 g, 21.3 mmol) was added. The reaction was allowed to stir at room temperature overnight. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined extracts were washed with saturated NaHCO3, 2N HCl, brine and dried with MgSO4. The mixture was filtered, concentrated in vacuo, and purified by silica gel chromatography (25-100% EtOAc in hexanes) to give the N′-(1-benzyloxy-carbonylamino-cyclopropyl)-hydrazinecarboxylic acid tert-butyl ester (6.2 g, 17.7 mmol) as a white solid, m/z 250.6 [M−101]+.

Aufarbeitung

  1. stirringto stir at room temperature overnight
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined extracts were washed with saturated NaHCO3, 2N HCl, brine
  4. dry with materialdried with MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (25-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-586980b88d01402ea2efb0e4950b4ec7
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552205B2

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