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Hydrochloric Acid → (S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[2-(1,1-dimethylethoxy)-2-oxoethyl]-benzenepropanoic acid

HRID 487799
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 487799
C[O:2][C:3](=[O:28])[C@@H:4]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][CH:7]=1.Cl>CO.[OH-].[Na+].CCOCC>[CH3:26][C:24]([CH3:27])([O:23][C:21]([NH:20][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][CH:7]=1)[C:3]([OH:28])=[O:2])=[O:22])[CH3:25]
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Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 14560606HCID 14560606, Verbindung

Produkt 1

HCID 14560610(S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[2-(1,1-dimethylethoxy)-2-oxoethyl]-benzenepropanoic acidAusbeute 77,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl Ether
Lösungsmittel
HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 1.471 g of (S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[2-(1,1-dimethylethoxy) -2-oxoethyl]benzenepropanoic acid methyl ester in 25 mL of methanol and 5 mL of 1N sodium hydroxide solution was stirred at room temperature for 2 hours. The mixture was acidified with a slight excess of hydrochloric acid, was diluted with 100 mL of ether, and was washed with water and saturated sodium chloride solution. The residue obtained after filtration and evaporation was chromatographed over 100 g of silica gel, eluting with 40:59:0.5 ethyl acetate-hexane-acetic acid. The product containing fractions were combined evaporated, diluted with toluene and evaporated finally under high vacuum to give 1.105 g of (S)-alpha-[[(1,1-dimethylethoxy) carbonyl]amino]-4-[2-(1,1-dimethylethoxy)-2-oxoethyl]benzene-propanoic acid [a]D +21.41 (ethanol).

Aufarbeitung

  1. washwas washed with water and saturated sodium chloride solution
  2. customThe residue obtained
  3. filtrationafter filtration and evaporation
  4. customwas chromatographed over 100 g of silica gel
  5. washeluting with 40:59:0.5 ethyl acetate-hexane-acetic acid
  6. additionThe product containing fractions
  7. customwere combined evaporated
  8. additiondiluted with toluene
  9. customevaporated finally under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4a1500bc9d1940c3b71b669d2fc4bd1e
Quelldatensatz
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05296608

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