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Sodium Hydroxide → Bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)

HRID 976043
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 976043
C[C:2]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]2[O:38][CH2:39][O:40][C:34]=2[CH:33]=1)([CH2:21][C:22]1[CH:27]=[CH:26][C:25]2[O:28][CH2:29][O:30][C:24]=2[CH:23]=1)[C:3]([NH:5][C@@:6]([CH3:20])([C:17]([OH:19])=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1.O.CCOCC>[CH2:39]1[O:38][C:35]2[CH:36]=[CH:37][C:32]([CH2:31][CH:2]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[C:3]([NH:5][C@@:6]([CH3:20])([C:17]([OH:19])=[O:18])[CH2:7][C:8]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[NH:10][CH:9]=3)=[O:4])=[CH:33][C:34]=2[O:40]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 2

HCID 14798Sodium HydroxideHCID 86750507Methyl bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)

Produkt 1

HCID 86750508Bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)Ausbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962
Water
Lösungsmittel
HCID 3283Diethyl EtherLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 0.36 g (0.66 mmol) of methyl bis-(3,4-methylenedioxyphenylmethyl)acetyl-(α-methyl-D-tryptophan) in 10 mL MeOH and 2 mL THF was treated with a solution of 0.133 g (3.3 mmol) of NaOH in 2 mL H2O and the solution stirred at room temperature for 2 days. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed twice with 1N HCl, then saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure gave the product. This was dissolved in Et2O and the solvent removed under reduced pressure to give 0.28 g (82.3% yield) of the product as an amorphous white solid. The structure was confirmed by NMR and mass spectroscopy.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. washwashed twice with 1N HCl
  3. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  4. customgave the product
  5. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3b4a85a92b9e4024a45c2487b4a94c20
Quelldatensatz
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05610177

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