Hydrochloric Acid → (R)-2-Amino-3-(thiazol-4-YL)propanoic acid

HRID 1379332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1379332
Cl.CC(C)(OC([NH:8][C@H:9]([CH2:13][C:14]1[N:15]=[CH:16][S:17][CH:18]=1)[C:10]([OH:12])=[O:11])=O)C>O1CCOCC1>[NH2:8][C@H:9]([CH2:13][C:14]1[N:15]=[CH:16][S:17][CH:18]=1)[C:10]([OH:12])=[O:11]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 7020917Boc-D-4-Thiazolylalanine

Produkt 1

HCID 7020912(R)-2-Amino-3-(thiazol-4-YL)propanoic acidAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of 4N hydrochloric acid in dioxane (10 ml) was added to a solution of (R)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(4-thiazolyl)propanoic acid (2.0 g, 7.3 mmol) in dioxane (2 ml). The reaction mixture was stirred at room temperature for 3 hours, concentrated in vacuo and the residue was dissolved in water (3 ml). The pH was adjusted to 6.5 with 1N sodium hydroxide and this solution was passed through 20 ml of Dowex® AG50(H+). The column was eluted with water (250 ml) followed by 2% pyridine in water (300 ml). The product containing fractions were concentrated in vacuo to yield 0.94 g of title product.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was dissolved in water (3 ml)
  3. washThe column was eluted with water (250 ml)
  4. additionThe product containing fractions
  5. concentrationwere concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d2c548e853074c549b52591995679074
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05670699

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