Dicyclohexylcarbodiimide → HCID 46840422, Verbindung

HRID 469454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469454
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][CH:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12]([OH:14])=[O:13])=[O:4].N1(O)C2C=CC=CC=2N=N1.[N:31]12[CH2:38][CH2:37][CH:34]([CH2:35][CH2:36]1)[C@@H:33](O)[CH2:32]2.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[O:13]=[C:12]([O:14][C@@H:33]1[CH:34]2[CH2:37][CH2:38][N:31]([CH2:36][CH2:35]2)[CH2:32]1)[CH:11]([NH:10][C:9]1[CH:8]=[CH:7][S:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 58557000HCID 58557000, Verbindung

Produkt 1

HCID 46840422HCID 46840422, VerbindungAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetic acid (I10) (700 mg, 2.40 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (487 mg, 3.60 mmol), (R)-quinuclidin-3-ol (458 mg, 3.60 mmol), and DCC (744 mg, 3.60 mmol) in dry THF (20 ml) was stirred at room temperature overnight. THF was evaporated, the crude product was partitioned between DCM and 2M K2CO3. The organic phase was collected, dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash-chromatography (DCM/MeOH=95/5) to obtain methyl 3-(2-oxo-1-phenyl-2-((R)-quinuclidin-3-yloxy)ethylamino)thiophene-2-carboxylate (302 mg, 31.4% yield).

Aufarbeitung

  1. customTHF was evaporated
  2. customthe crude product was partitioned between DCM and 2M K2CO3
  3. customThe organic phase was collected
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude was purified by flash-chromatography (DCM/MeOH=95/5)

Quellen und Nachweise

ORD-Eintrag
ord-2e160929dda0454fa2c95fe8465242e1
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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