Citric Acid → (R)-tert-butyl (2-hydroxy-1-(4-hydroxyphenyl)ethyl)carbamate

HRID 454971

Reaktionsgleichung

Reaktionsgleichung von HRID 454971
C[O:2][C:3](=O)[C@H:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.B.[Li].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:16]([O:15][C:13](=[O:14])[NH:12][C@H:4]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH2:3][OH:2])([CH3:19])([CH3:17])[CH3:18]

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 10934864Methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-(4-hydroxyphenyl)acetateHCID 178419226HCID 178419226, Verbindung

Produkt 1

HCID 67073553(R)-tert-butyl (2-hydroxy-1-(4-hydroxyphenyl)ethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(R)-tert-Butoxycarbonylamino-(4-hydroxy-phenyl)-acetic acid methyl ester (10 mmol), Lithium Boron hydride (1.089 g, 50 mmol) and THF (50 ml) were combined and stirred at room temperature overnight. Ice (20 ml) was added into the reaction mixture with stirring. Saturated citric acid was then added dropwise until no more bubbles were generated. The reaction mixture was transferred to a separatory funnel. The aqueous layer was extracted with ethyl acetate (3×30 ml). The combined organic layers were washed with saturated NH4Cl and water sequentially, then dried over MgSO4, filtered and concentrated to give a white crude solid (2.92 g, crude product) with some impurity: 1H NMR (400 MHz, MeOD) δ ppm 7.14 (d, J=8.6 Hz, 2H), 6.76 (d, J=8.6 Hz, 2H), 4.56 (m, 1H), 3.63 (m, 2H), 1.43 (s, 9H); LCMS (ESI) m/e 254.1 [(M+H)+, calcd for C13H20NO4 254.3].

Aufarbeitung

  1. stirringwith stirring
  2. customThe reaction mixture was transferred to a separatory funnel
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×30 ml)
  4. washThe combined organic layers were washed with saturated NH4Cl and water sequentially
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a white crude solid (2.92 g, crude product) with some impurity

Quellen und Nachweise

ORD-Eintrag
ord-ce7005a1ecff4913a3d6285bed6bfa2d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497271B2

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