Ethyl Acetate → Pivaloyloxymethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylate

HRID 52881

Reaktionsgleichung

Reaktionsgleichung von HRID 52881
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:31]([C:32]([OH:34])=[O:33])=[C:30]([CH2:35][OH:36])[N:29]=[C:28]2[CH2:37][CH2:38][CH2:39][CH3:40])=[CH:22][CH:21]=1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[C:41]([O:47][CH2:48]Cl)(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43].C(OCC)(=O)C>CN(C)C(=O)C.O>[C:41]([O:47][CH2:48][O:33][C:32]([C:31]1[N:27]([CH2:26][C:23]2[CH:24]=[CH:25][C:20]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])=[CH:21][CH:22]=2)[C:28]([CH2:37][CH2:38][CH2:39][CH3:40])=[N:29][C:30]=1[CH2:35][OH:36])=[O:34])(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 190361191-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylic acid

Produkt 1

HCID 19036181Pivaloyloxymethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylateAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

350 mg of potassium carbonate were added to a solution of 552 mg of 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylic acid (prepared as described in Example 4) and 220 mg of pivaloyloxymethyl chloride in 7 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 5 hours. At the end of this time, the reaction mixture was mixed with ethyl acetate and water, and the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate; the solvent was then removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to give 0.62 g of the title compound as a syrup.

Aufarbeitung

  1. customthe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was then removed by distillation under reduced pressure
  4. customThe resulting residue was purified by column chromatography through silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b64c46f517f34819a0036b46f94e10df
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616599

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