Dichloromethane → (2S)-2-(t-butoxycarbonylamino)-3-[4-(1-methyluracil-3-yl)phenyl]propionic acid

HRID 253684

Reaktionsgleichung

Reaktionsgleichung von HRID 253684
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][N:24]1[CH:31]=[CH:30][C:28](=[O:29])[NH:27][C:25]1=[O:26].C(N(CC)CC)C.ClCCl>C(O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:27]2[C:28](=[O:29])[CH:30]=[CH:31][N:24]([CH3:23])[C:25]2=[O:26])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 120091-MethyluracilHCID 58746869[(S)-3-(4-boronophenyl)-2-((tertbutoxycarbonyl)amino)propanoic acid]

Produkt 1

HCID 66839695(2S)-2-(t-butoxycarbonylamino)-3-[4-(1-methyluracil-3-yl)phenyl]propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The mixture of 30 mg of (2S)-2-(t-butoxycarbonylamino)-3-[4-(dihydroxy boranyl)phenyl]propionic acid, 25 mg of 1-methyluracil, 27 mg of copper acetate(II), 40 mg of triethylamine and 4 ml of dichloromethane were stirred overnight. The reaction solvent was diluted by ethanol and filtered by Celite filtration. The residual material obtained by concentrating the filtrate was dilluted by 1N sodium hydroxide and washed with ethyl acetate. After making the water layer acidic by hydrochloric acid, the solution was extracted with ethyl acetate, washed with saturated NaCl aqueous solution, dried with magnesium sulfate and the solvent was removed to obtain a crude material of (2S)-2-(t-butoxycarbonylamino)-3-[4-(1-methyluracil-3-yl)phenyl]propionic acid. This crude material was diluted by 5 ml of ethanol and hexane solution including 2M trimethylsilyldiazomethane was added to give methyl ester. The reaction solvent was concentrated and purified by silica gel chromatography (ethyl acetate-ethanol) to obtain the title compound (7 mg).

Aufarbeitung

  1. filtrationfiltered by Celite filtration
  2. customThe residual material obtained
  3. concentrationby concentrating the filtrate
  4. washwashed with ethyl acetate
  5. extractionthe solution was extracted with ethyl acetate
  6. washwashed with saturated NaCl aqueous solution
  7. dry with materialdried with magnesium sulfate
  8. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-3f9dc6a6981a4515ac5fa99ae75e6cf0
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872125B2

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