Trifluoroacetic acid → 2-Amino-3-(1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl ester

HRID 1353558

Reaktionsgleichung

Reaktionsgleichung von HRID 1353558
[CH3:1][O:2][C:3](=[O:30])[CH:4]([N:15](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][N:13]=[CH:14][C:8]=2[CH2:7]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:30])[CH:4]([NH2:15])[CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][N:13]=[CH:14][C:8]=2[CH2:7]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 588643312-(Di-tert-butoxycarbonylamino)-3-(1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl ester

Produkt 1

HCID 588644802-Amino-3-(1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(di-tert-butoxycarbonylamino)-3-(1,4,6,7-tetrahydro-pyrazolo-[4,3-c]pyridin-5-yl)-propionic acid methyl ester (0.55 g, 1 equiv.) in methylene chloride (5 mL, 0° C.) was added trifluoroacetic acid (1.5 mL). The ice bath was removed and stirring continued for 2 h. The solution was concentrated, redissolved in methanol, and passed onto a column of strong cation exchange resin. After flushing with methanol, the product was removed from the column by eluting with 2 M ammonia in methanol to afford the product as its free base (275 mg, 95%). 1H-NMR (CDCl3, 500 MHz) δ 2.71 (dd, J=12.8, 8.6, 1H), 2.74–2.91 (m, 6H), 3.48 (s, 2H), 3.54 (d, J=13.4, 1H), 3.62 (d, J=13.4, 1H), 3.69 (dd, J=8.2, 4.9, 1H), 3.73 (s, 3H), 7.27 (s, 1H). Mass spec.: 225.16 (MH)+.

Aufarbeitung

  1. customThe ice bath was removed
  2. concentrationThe solution was concentrated
  3. dissolutionredissolved in methanol
  4. customAfter flushing with methanol
  5. customthe product was removed from the column
  6. washby eluting with 2 M ammonia in methanol

Quellen und Nachweise

ORD-Eintrag
ord-58d21544437b4a6bb16c54120b4a59e4
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220862B2

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