Ethyl Acetate → tert-Butyl{(1R)-2-[(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)oxy]-1-phenylethyl}carbamate

HRID 1038974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038974
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[NH2:25])[O:5][CH2:6][C@H:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1N=CN([C:31](N2C=NC=C2)=[O:32])C=1.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[O:32]=[C:31]1[NH:25][C:24]2[CH:23]=[CH:22][C:4]([O:5][CH2:6][C@H:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:3][C:2]=2[NH:1]1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 58443062tert-butyl [(1R)-2-(3,4-diaminophenoxy)-1-phenylethyl]carbamate2×

Produkt 1

HCID 68240928tert-Butyl{(1R)-2-[(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)oxy]-1-phenylethyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

tert-Butyl [(1R)-2-(3,4-diaminophenoxy)-1-phenylethyl]carbamate (Intermediate 6) (318 mg, 0.93 mmol) was placed in a 50-mL RBF under a nitrogen atmosphere and dissolved in DMF (5 mL). CDI (135 mg, 0.83 mmol) was added, and the reaction was stirred at room temperature for four hours. The reaction was added to a separatory funnel containing ethyl acetate (125 mL) and dilute aqueous NaHCO3 (75 mL); the phases were separated, and the organic layer was washed with brine (75 mL), dried over anhydrous Na2SO4 and then concentrated in vacuo. The crude product mixture was then purified by silica gel chromatography to afford tert-butyl {(1R)-2-[(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)oxy]-1-phenylethyl}carbamate as a white solid. 1H NMR (500 MHz, C2D6SO) δ 10.49 (s, 1H), 10.37 (s, 1H), 7.54 (d, 1H), 7.34 (m, 4H), 7.25 (t, 1H), 6.77 (d, 1H), 6.48 (s, 2H), 4.86 (q, 1H), 3.98 (m, 2H), 1.37 (s, 9H). LRMS (ESI) calc'd for (C16H16N3O4) [M−C4H8+H]+, 314.1; found 314.1.

Aufarbeitung

  1. additionThe reaction was added to a separatory funnel
  2. customthe phases were separated
  3. washthe organic layer was washed with brine (75 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product mixture was then purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-197479e5642643c6b4a7bc3d6844d74c
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552019B2

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