benzyl trifluoroacetyl-L-serinate → benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinate

HRID 2165233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2165233
[C:1]([O:4][C@H:5]([CH3:21])[C@@H:6]([C:18]([OH:20])=[O:19])[NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])(=[O:3])[CH3:2].[F:22][C:23]([F:41])([F:40])[C:24]([NH:26][C@H:27]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:28]O)=[O:25]>C(Cl)Cl>[C:1]([O:4][C@H:5]([CH3:21])[C@H:6]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:18]([O:20][CH2:28][C@@H:27]([C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])[NH:26][C:24](=[O:25])[C:23]([F:22])([F:40])[F:41])=[O:19])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 14357546benzyl trifluoroacetyl-L-serinateHCID 18640002O-acetyl-N-benzyloxycarbonyl-L-threonine

Produkt 1

HCID 18639967benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinateAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of O-acetyl-N-benzyloxycarbonyl-L-threonine (1 g) and benzyl N-trifluoroacetyl-L-serinate (987 mg) in methylene chloride (20 ml) was added N,N-diethylaminopropyl-N'-ethylcarbodiimide hydrochloride (1.22 g) and 4-N,N-dimethylaminopyridine (77.8 mg) at room temperature. After stirring for an hour at room temperature, the reaction mixture was washed successively with aqueous hydrogen chloride, water, 10% aqueous sodium hydrogen carbonate and brine. After drying over sodium sulfate, the methylene chloride extract was filtered and concentrated. The residue was chromatographed on silica gel (20 g) eluting successively with a mixture of hexane and methylene chloride (1:1), methylene chloride and a mixture of methylene chloride and acetone (125:1) to give benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxo-butyl]-N-trifluoroacetyl-L-serinate (1.42 g).

Aufarbeitung

  1. washthe reaction mixture was washed successively with aqueous hydrogen chloride, water, 10% aqueous sodium hydrogen carbonate and brine
  2. dry with materialAfter drying over sodium sulfate
  3. extractionthe methylene chloride extract
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (20 g)
  7. washeluting successively with a mixture of hexane and methylene chloride (1:1), methylene chloride
  8. additiona mixture of methylene chloride and acetone (125:1)

Quellen und Nachweise

ORD-Eintrag
ord-1059afd4609c49ac9334cb5a4acaa2ca
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04939241

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