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Triethylamine → (2RS,3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid

HRID 1722905
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1722905
[NH2:1][C@@H:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]([OH:7])[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[C:19]([O:23][C:24](ON=C(C1C=CC=CC=1)C#N)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O.O1CCOCC1>[C:19]([O:23][C:24]([NH:1][C@@H:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]([OH:7])[C:4]([OH:6])=[O:5])=[O:25])([CH3:22])([CH3:21])[CH3:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 12879199(2RS,3S)-3-amino-2-hydroxy-5-methylhexanoic acid

Produkt 1

HCID 13848631(2RS,3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acidAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962Water
Lösungsmittel
2×
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3.22 g of (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoic acid and 3.08 ml of triethylamine in 30 ml of water was added a solution of 5.41 g of 2-(tert-butyloxycarbonyloxyimino)-2-phenylacetonitrile in 30 ml of dioxane, and the mixture was stirred for 16 hours at room temperature. To the reaction mixture was added 100 ml of water, and the mixture was extracted with ethyl acetate to remove neutral materials. The aqueous layer was acidified by the addition of an aqueous citric acid solution, and the acid solution was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 5.10 g of (2RS,3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid as a pale yellow oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. customto remove neutral materials
  3. additionThe aqueous layer was acidified by the addition of an aqueous citric acid solution
  4. extractionthe acid solution was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c128414d6a804fed8f8b04332b070d63
Quelldatensatz
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04857650

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