Diisopropylethylamine → [1-(1-Oxazol-4-yl-cyclopropylcarbamoyl)-cyclopropyl]-carbamic acid benzyl ester

HRID 1040449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040449
[CH2:1]1[C:3]([NH:7][C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])([C:4]([OH:6])=O)[CH2:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:51]1[CH:55]=[C:54]([C:56]2([NH2:59])[CH2:58][CH2:57]2)[N:53]=[CH:52]1>CN(C=O)C>[CH2:11]([O:10][C:8](=[O:9])[NH:7][C:3]1([C:4](=[O:6])[NH:59][C:56]2([C:54]3[N:53]=[CH:52][O:51][CH:55]=3)[CH2:58][CH2:57]2)[CH2:2][CH2:1]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 35890121-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 552855321-Oxazol-4-yl-cyclopropylamine

Produkt 1

HCID 67391472[1-(1-Oxazol-4-yl-cyclopropylcarbamoyl)-cyclopropyl]-carbamic acid benzyl esterAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a round bottom flask was added Z-1-aminocyclopropane-1-carboxylic acid (150 mg, 0.638 mmol) in DMF (10 ml), followed by the addition of Hunig's base (207 mg, 1.6 mmol) and HATU (270 mg, 0.71 mmol). The reaction mixture was stirred at room temperature for 15 min, followed by the addition of 1-Oxazol-4-yl-cyclopropylamine (200 mg, 1.6 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo. The residue was purified by prepHPLC to afford 70 mg of [1-(1-oxazol-4-yl-cyclopropylcarbamoyl)-cyclopropyl]-carbamic acid benzyl ester, m/z 343 [M+1]+.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 18 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by prepHPLC

Quellen und Nachweise

ORD-Eintrag
ord-3605e290fdad42349ab63b3a6f26d669
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552205B2

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