Benzyltrimethylammonium hydroxide → 3-(3-1,2-Benzisoxazol-3-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester

HRID 1747357

Reaktionsgleichung

Reaktionsgleichung von HRID 1747357
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]2=[O:20])=[N:2]1.[C:21]([O:28][CH2:29][CH3:30])(=[O:27])/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH3:26].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CN(C=O)C.[NH4+].[Cl-]>[CH2:29]([O:28][C:21](=[O:27])[CH2:22][CH:23]([N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:11]([CH2:10][C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[O:1][N:2]=2)[C:12]1=[O:20])[CH2:24][CH2:25][CH3:26])[CH3:30]

Komponenten

6

Edukt 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 5364778Ethyl trans-2-hexenoateHCID 594976021-1,2-Benzisoxazol-3-ylmethyl-1,3-dihydro-benzimidazol-2-one

Produkt 1

HCID 594973183-(3-1,2-Benzisoxazol-3-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl esterAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of 1-1,2-benzisoxazol-3-ylmethyl-1,3-dihydro-benzimidazol-2-one (100 mg, 0.38 mmol) in DMF (5 ml) was added ethyl trans-2-hexenoate (80 mg, 0.57 mmol) followed by benzyltrimethylammonium hydroxide (Triton B, 40 wt % in MeOH, 17.0 ul). The resulting mixture was warmed to 60° C. for 12 h and cooled to ambient temperature. The reaction was diluted with NH4Cl (sat.) and the product was extracted into ethyl acetate (2×). The combined organics were dried (MgSO4), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 5% EtOAc/dichloromethane). The product-containing fractions were combined and concentrated to give 70 mg (46%) of the desired product.

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. extractionthe product was extracted into ethyl acetate (2×)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified via column chromatography (silica gel, 5% EtOAc/dichloromethane)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1f6ce19c6ca245a2bce6eeb1e70ff29f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

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