Tetrahydrofuran → N-Boc-4-chloro-3-fluoro-D-phenylalanine

HRID 1675832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1675832
O[Li].O.[C:4]([O:8][C:9]([NH:11][C@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=1)[C:13]([O:15]C)=[O:14])=[O:10])([CH3:7])([CH3:6])[CH3:5].C1COCC1>O>[C:4]([O:8][C:9]([NH:11][C@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([F:25])[CH:19]=1)[C:13]([OH:15])=[O:14])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67338942(R)-methyl 2-(tert-butoxycarbonylamino)-3-(4-chloro-3-fluorophenyl)propanoate

Produkt 1

HCID 67340403N-Boc-4-chloro-3-fluoro-D-phenylalanineAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

LiOH—H2O (0.6246 g, 14.88 mmol) was added to a solution of (R)-methyl 2-(tert-butoxycarbonylamino)-3-(4-chloro-3-fluorophenyl)propanoate (1.646 g, 4.961 mmol) in 1:1 THF:H2O (26 mL). The reaction mixture was stirred at room temperature for 2 hours, after which it was diluted with H2O and washed with EtOAc. The aqueous layer was then acidified with solid KHSO4 and extracted with DCM. The combined extracts were dried (Na2SO4), filtered, concentrated, and then re-concentrated from DCM/hexanes to give (R)-2-(tert-butoxycarbonylamino)-3-(4-chloro-3-fluorophenyl)propanoic acid (1.31 g, 83.10% yield) as a white powder. LCMS (APCI−) m/z 316 [M−H]−.

Aufarbeitung

  1. washwashed with EtOAc
  2. extractionextracted with DCM
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationre-concentrated from DCM/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-16eda8ef798c4b458c04f97c2d7e42e1
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003651B2

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