Diisopropylethylamine → (Tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-1,1-dimethyl-ethoxycarbonylamino)-acetic acid

HRID 1893651

Reaktionsgleichung

Reaktionsgleichung von HRID 1893651
[NH2:1][CH:2]([CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)[C:3]([OH:5])=[O:4].[F:12][C:13]([F:31])([F:30])[C:14]([O:17][C:18](=O)[O:19]C1C=CC([N+]([O-])=O)=CC=1)([CH3:16])[CH3:15].CCN(C(C)C)C(C)C>CC#N.O>[O:9]1[CH2:8][CH2:7][CH:6]([CH:2]([NH:1][C:18]([O:17][C:14]([CH3:16])([CH3:15])[C:13]([F:31])([F:30])[F:12])=[O:19])[C:3]([OH:5])=[O:4])[CH2:11][CH2:10]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 33855454'-TetrahydropyranylglycineHCID 577851834-Nitrophenyl 1,1,1-Trifluoro-2-Methylpropan-2-yl-carbonate

Produkt 1

HCID 68797736(Tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-1,1-dimethyl-ethoxycarbonylamino)-acetic acidAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Amino-(tetrahydro-pyran-4-yl)-acetic acid (80 mg, 0.5 mmol) was dissolved in CH3CN (5 mL) and H2O (1 mL), carbonic acid 4-nitro-phenyl ester 2,2,2-trifluoro-1,1-dimethyl-ethyl ester (175 mg, 0.6 mmol) and DIEA (88 μL, 0.5 mmol) were added slowly. The reaction 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 (tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-1,1-dimethyl-ethoxycarbonylamino)-acetic acid as light yellow solid (110 mg, 70%).

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-89b536c7f34946ba950dfce2f1f3c7ad
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513186B2

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