Hydrochloric Acid → trans-4-Aminomethyl-L-Proline 4-Phenoxyphenylamide Dihydrochloride

HRID 2185464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185464
[ClH:1].[O:2]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:38])[C@@H:17]2[CH2:21][C@@H:20]([CH2:22][NH:23]C(OC(C)(C)C)=O)[CH2:19][N:18]2C(OC(C)(C)C)=O)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[ClH:1].[ClH:1].[O:2]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:38])[C@@H:17]2[CH2:21][C@@H:20]([CH2:22][NH2:23])[CH2:19][NH:18]2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 54074172trans-4-(N-tert-Butoxycarbonylaminomethyl)-N-tert-Butoxycarbonyl-L-Proline 4-Phenoxyphenylamide

Produkt 1

HCID 70177808trans-4-Aminomethyl-L-Proline 4-Phenoxyphenylamide Dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of 4 N hydrochloric acid in 1,4-dioxane (6 mL) was added to a solution of trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-L-proline 4-phenoxyphenylamide (A, 182 mg) in 1,4-dioxane (6 mL) at room temperature. After stirring at room temperature for 20 min, the reaction mixture was concentrated in vacuo. The residue was washed with ether to give the title compound (95 mg) as a colorless solid: 1H NMR (400 MHz, D2O) δ 2.36 (m, 1 H), 2.60 (m, 1H), 2.82 (m, 1 H), 3.23 (m, 3 H), 3.85 (dd, J=7.5, 11.5 Hz, 1 H), 4.73 (dd, J=3.9, 9.3 Hz, 1 H), 7.08 (d, J=6.84 Hz, 2 H), 7.10 (d, J=6.84 Hz, 2 H), 7.22 (t, J=7.0 Hz, 1H), and 7.45 (m, 4 H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washThe residue was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-e34185bc89254a8aad2590bb2fe839bf
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399629B1

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