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Hydrochloric Acid → (1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate Hydrochloride

HRID 2421547
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2421547
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:26]C(OC(C)(C)C)=O)[C:11]([O:13][C@H:14]([CH3:25])[CH2:15][O:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[ClH:34]>O1CCOCC1>[ClH:34].[NH2:26][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][C@H:14]([CH3:25])[CH2:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18])=[O:12]
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 60207245(1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate

Produkt 1

HCID 60207241(1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate HydrochlorideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate (1.87 g, 4 mmol) was dissolved in 40 mL of 4M HCl in dioxane. The resulting mixture was stirred at room temperature for 30 min. Dioxane was evaporated completely under reduced pressure. The resulting white solid was dissolved in acetonitrile (5 mL), and ether added until the solution became slightly cloudy. The solution was refrigerated overnight and the product was crystallized. The white crystalline solid was collected and dried under vacuum to afford 1.5 g (93%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 1.35 (d, J=6.4 Hz, 3H), 3.01 (dd, J=6.8, 14.4 Hz, 1H), 3.08 (dd, J=6.4, 14.4 Hz, 1H), 4.19 (t, J=6.4 Hz, 1H), 4.34 (dd, J=6, 12.4 Hz, 1H), 4.49 (dd, J=2.8, 12.4 Hz, 1H), 5.35 (m, 1H), 6.55 (dd, J=2, 8 Hz, 1H), 6.66 (d, J=2 Hz, 1H), 6.71 (d, J=8 Hz, 1H), 7.48 (t, J=7.2 Hz, 2H), 7.61 (t, J=7.2 Hz, 1H), 8.02 (d, J=7.6 Hz, 2H). MS (ESI) m/z 360.16 (M+H)+ and 358.13 (M−H)−.

Aufarbeitung

  1. customDioxane was evaporated completely under reduced pressure
  2. dissolutionThe resulting white solid was dissolved in acetonitrile (5 mL)
  3. additionether added until the solution
  4. waitThe solution was refrigerated overnight
  5. customthe product was crystallized
  6. customThe white crystalline solid was collected
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-06448296e96643ea98bd2a6d828dcaeb
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07956212B2

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