Water → HCID 66749849, Verbindung

HRID 2405808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2405808
[NH2:1][CH:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].O.[O:11]1[CH2:15][CH2:14][CH:13]([O:16][C:17](=O)[O:18]C2C=CC([N+]([O-])=O)=CC=2)[CH2:12]1.CCN(C(C)C)C(C)C>CC#N.CO>[CH3:7][C:6]([CH3:9])([CH3:8])[CH:2]([NH:1][C:17]([O:16][CH:13]1[CH2:14][CH2:15][O:11][CH2:12]1)=[O:18])[C:3]([OH:5])=[O:4]

Komponenten

7

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 3061312-Amino-3,3-dimethylbutanoic acidHCID 15343685HCID 15343685, Verbindung

Produkt 1

HCID 66749849HCID 66749849, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Amino-3,3-dimethyl-butyric acid (551 mg, 4.2 mmol) was dissolved in CH3CN (15 mL), H2O (3 mL) and MeOH (3 mL). Carbonic acid 4-nitro-phenyl ester tetrahydro-furan-3-yl ester (1.6 g, 6.3 mmol) and DIEA (1.46 mL, 8.4 mmol) were added. This reaction mixture was allowed to stir at room temperature for 16 h. After concentrated, diluted with EtOAc, washed with brine and H2O, dried over Na2SO4, the crude product was purified on silica (12 g, 25-75% EtOAc/hexanes) to give intermediate 3,3-dimethyl-2-(tetrahydro-furan-3-yloxycarbonylamino)-butyric acid as a white solid (670 mg, 65%).

Aufarbeitung

  1. concentrationAfter concentrated
  2. additiondiluted with EtOAc
  3. washwashed with brine and H2O
  4. dry with materialdried over Na2SO4
  5. customthe crude product was purified on silica (12 g, 25-75% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5028264ea5cf4a0db96bef74e48473cf
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809267B2

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