Hydrochloric Acid → 2-((R)-3-Amino-4-hydroxy-but-1-enyl)-benzoic Acid Ethyl Ester

HRID 660560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660560
C(OC([N:8]1[C@H:12]([CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl>CO>[CH2:24]([O:23][C:21](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:14]=[CH:13][C@@H:12]([NH2:8])[CH2:11][OH:10])[CH3:25]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68839236(R)-4-[2-(2-Ethoxycarbonylphenyl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic Acid Tert-butyl Ester

Produkt 1

HCID 688421982-((R)-3-Amino-4-hydroxy-but-1-enyl)-benzoic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (R)-4-[2-(2-ethoxycarbonylphenyl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (3.3 g, 8.70 mmol) in methanol (50 mL) is added conc. HCl (4 mL) and stirred at RT for 18 h. The solvent is removed under reduced pressure and EtOAc and 2N NaOH, which is saturated by NaCl, is added. The aqueous phase is extracted with EtOAc and the organic phases are combined together, washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound as a white solid: (M+1)+=236.

Aufarbeitung

  1. customThe solvent is removed under reduced pressure and EtOAc and 2N NaOH, which
  2. additionis added
  3. extractionThe aqueous phase is extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-940237320dd94f64bc2d1c378ee02472
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084448B2

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