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Acetonitrile → 2-(((Benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)propanoic acid

HRID 12403
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 12403
[CH2:1]([O:8][C:9]([NH:11]C(C(O)=O)CC(=O)N)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](OCC)(=O)C.[C:26](#[N:28])C.[C:29]([OH:32])(=[O:31])[CH3:30].[C:33]([OH:36])(=[O:35])C.I([C:39]1[CH:44]=[CH:43]C=CC=1)=O>O>[CH2:1]([O:8][C:9]([NH:11][CH:30]([CH2:26][NH:28][C:33]([O:36][C:44]([CH3:43])([CH3:39])[CH3:20])=[O:35])[C:29]([OH:32])=[O:31])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 246565Carbobenzoxy-L-asparagineHCID 73357407Acetic acid;iodosylbenzene

Produkt 1

HCID 41154162-(((Benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

To N-(benzyloxycarbonyl)-DL-asparagine (7.5 g) were added ethyl acetate (36 ml), acetonitrile (36 ml), water (18 ml) and iodosobenzene diacetate (10 g), and the mixture was stirred overnight at room temperature. The reaction mixture was filtered and, after washing the obtained solid with ethyl acetate, dioxane (180 ml), water (40 ml), 1N aqueous sodium hydroxide solution (10 ml) and di-t-butyl dicarbonate (6.1 g) were added, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with 0.5N hydrochloric acid. The solvent was evaporated to give 2-benzyloxycarbonylamino-3-tert-butoxycarbonylaminopropionic acid as a crude product. The crude product was treated in the same manner as in Step 1 of Example 15 to give (2-benzyloxycarbonylamino-3-hydroxypropyl)carbamic acid tert-butyl ester (2 g).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washafter washing the obtained solid with ethyl acetate, dioxane (180 ml), water (40 ml), 1N aqueous sodium hydroxide solution (10 ml) and di-t-butyl dicarbonate (6.1 g)
  3. additionwere added
  4. stirringthe mixture was stirred overnight at room temperature
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. washwashed with 0.5N hydrochloric acid
  7. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-090ebc008d494b28bcd771d148fefc56
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728005B2

Notizen zur Reaktion

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