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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86700688, Verbindung

HRID 1406870
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1406870
[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]1[O:19]C(C2CCNCC2)=N[N:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:31]=[C:32]=[N:33]CCCN(C)C.C1C=CC2N(O)N=NC=2C=1.ONC(N)=N>CN(C=O)C.O>[NH2:33][C:32]1[N:22]=[C:18]([C@@H:13]2[CH2:12][CH2:11][C@@H:10]3[CH2:17][N:14]2[C:15](=[O:16])[N:9]3[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:19][N:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 86700689HCID 86700689, VerbindungHCID 178513189HCID 178513189, Verbindung

Produkt 1

HCID 86700688HCID 86700688, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (2S,5R)-6-(benzyloxy)-2-(5-(piperidin-4-yl)-1,3,4-oxadiazol-2-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (2.0 g, 7.25 mmol), EDCI (1.53 g, 7.98 mmol) and HOBT (1.08 g, 7.98 mmol) in DMF (15 mL) was stirred at rt for 0.5 h. 1-Hydroxyguanidine (0.653 g, 7.98 mmol) was then added and the reaction mixture was stirred for an additional 0.5 h. The resulting solution was treated under microwave at 100° C. for 1.5 hrs. The mixture was poured into water and extracted with EtOAc (2×). The combined organic layers were then washed with water (20 mL), and saturated sodium chloride (20 mL), dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (2:1 EtOAc/petroleum ether) to give (2S,5R)-2-(3-amino-1,2,4-oxadiazol-5-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one (1.0 g, 44%). (ESI-MS (EI+, m/z): 316 [M+H]+.

Aufarbeitung

  1. additionThe resulting solution was treated under microwave at 100° C. for 1.5 hrs
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were then washed with water (20 mL), and saturated sodium chloride (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (2:1 EtOAc/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-d3d85a93c60e4eb29540b4fced52d09e
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08916709B2

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