Hydrochloric Acid → 2-Hydroxy-3-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate hydrochloride

HRID 1698480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698480
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:27]C(OC(C)(C)C)=O)[C:11]([O:13][CH2:14][CH:15]([OH:26])[CH2:16][O:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[ClH:35]>O1CCOCC1>[ClH:35].[NH2:27][C@@H:10]([CH2:9][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=1)[C:11]([O:13][CH2:14][CH:15]([OH:26])[CH2:16][O:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19])=[O:12]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 602072522-Hydroxy-3-phenylcarbonyloxypropyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate

Produkt 1

HCID 574622892-Hydroxy-3-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate hydrochlorideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-Hydroxy-3-phenylcarbonyloxypropyl(2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate (2.05 g, 4.3 mmol) was treated with 4.0M HCl in 1,4-dioxane at room temperature for 30 min. The reaction mixture was concentrated to dryness under reduced pressure and purified by prep-HPLC. The HPLC fractions were pooled, treated with 10 mL of 0.5N HCl, and dried by lyophilization to yield 0.85 g (48%) of the title compound as a white solid. 1H NMR (400 MHz, D2O): δ 3.11 (t, J=6.6 Hz, 2H), 4.38-4.44 (m, 6H), 6.60 (dd, J=2.2, 7.8 Hz, ½H), 6.61 (dd, J=2.4, 8.0 Hz, ½H), 6.70 (d, J=2.0 Hz, ½H), 6.71 (d, J=2.0 Hz, ½H), 6.77 (d, J=8.0 Hz, ½H), 6.78 (d, J=8.0 Hz, ½H), 7.46-7.52 (m, 2H), 7.60-7.68 (m, 1H), 7.96-8.02 (m, 2H); MS (ESI) m/z 376.15 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. custompurified by prep-HPLC
  3. additiontreated with 10 mL of 0.5N HCl
  4. customdried by lyophilization

Quellen und Nachweise

ORD-Eintrag
ord-35f7678dee264bc09d5efc1be6331990
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163958B2

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