Triethylamine → HCID 178453727, Verbindung

HRID 46132

Reaktionsgleichung

Reaktionsgleichung von HRID 46132
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH3:22])([CH2:15][CH:16]2CCNCC2)[C:12](=[O:14])[N:13]=1.[C:23]([NH:30][CH2:31][CH2:32][O:33][C:34]1[CH:42]=[CH:41][C:37](C(O)=O)=[CH:36][CH:35]=1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].CCN=C=NCCCN(C)C.C1C=CC2N([OH:63])N=NC=2C=1.[CH2:64]([N:66]([CH2:69][CH3:70])[CH2:67][CH3:68])C>C(Cl)Cl>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH2:15][CH:16]2[CH2:70][CH2:69][N:66]([C:64]([C:41]3[CH:42]=[C:34]([CH:35]=[CH:36][CH:37]=3)[O:33][CH2:32][CH2:31][NH:30][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:63])[CH2:67][CH2:68]2)([CH3:22])[C:12](=[O:14])[N:13]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27559974-(2-((tert-Butoxycarbonyl)amino)ethoxy)benzoic acidHCID 178422083HCID 178422083, Verbindung

Produkt 1

HCID 178453727HCID 178453727, VerbindungAusbeute 412,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-5-(piperidin-4-ylmethyl)thiazol-4(5H)-one (534 mg, 1.66 mmol), 4-[2-(Boc-amino)ethyloxy]-benzoic acid (NeoMPS, 701 mg, 2.49 mmol), EDCI (Aldrich, 637 mg, 3.32 mmol, 2.0 eq), HOBt (Aldrich, 45 mg, 0.332 mmol, 0.2 eq) and triethylamine (Aldrich, 336 mg, 3.32 mmol, 2.0 eq) in CH2Cl2 (10 mL) was stirred at room temperature for ca. 18 h. The reaction was quenched with saturated NaHCO3 (100 mL), and the crude product was extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Flash column chromatography (silica gel, 0-5% MeOH in CH2Cl2) afforded the title compound as a white solid (800 mg). MS (ESI, pos. ion) m/z: 585 (M+H).

Aufarbeitung

  1. customThe reaction was quenched with saturated NaHCO3 (100 mL)
  2. extractionthe crude product was extracted with CH2Cl2 (3×100 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8abc0d1e58874940854250353656a801
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541592B2

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