Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[4-(3-fluoropropoxy)benzyl]-D-glutamate → (4R)-4-[4-(3-Fluoropropoxy)benzyl]-D-glutamic acid

HRID 591295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591295
C(OC([NH:8][C@@H:9]([C:31]([O:33]C(C)(C)C)=[O:32])[CH2:10][C@@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][F:30])=[CH:22][CH:21]=1)[C:12]([O:14]C(C)(C)C)=[O:13])=O)(C)(C)C>FC(F)(F)C(O)=O>[F:30][CH2:29][CH2:28][CH2:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][C@@H:11]([C:12]([OH:14])=[O:13])[CH2:10][C@H:9]([C:31]([OH:33])=[O:32])[NH2:8])=[CH:21][CH:22]=1

Komponenten

3

Edukt 1

HCID 70674428Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[4-(3-fluoropropoxy)benzyl]-D-glutamate

Produkt 1

HCID 70673992(4R)-4-[4-(3-Fluoropropoxy)benzyl]-D-glutamic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

60 mg (0.11 mmol) of di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-[4-(3-fluoropropoxy)-benzyl]-D-glutamate were taken up in 3 mL of trifluoro acetic acid and stirred overnight at room temperature. The excess of trifluoro acetic acid was evaporated and the residue was taken up three times in tetrahydrofuran and then evaporated. The resulting oil was chromatographed on C-18 reversed phase silica gel using a water/acetonitrile gradient, the appropriate fractions were combined and concentrated.

Aufarbeitung

  1. customThe excess of trifluoro acetic acid was evaporated
  2. customevaporated
  3. customThe resulting oil was chromatographed on C-18
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d0103b904c3549ee8b1831d5344eb722
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238631B2

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