Hydrochloric Acid → 2(R)-(3-(Acetylthio)-2(S)-methyl-1-oxopropoxy)-3-(methylthio)propanoic acid

HRID 2226575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226575
[C:1]([S:4][CH2:5][C@@H:6]([CH3:10])[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[C@@H:24]([CH2:28][S:29][CH3:30])[C:25]([OH:27])=[O:26].C(N(CC)CC)C.Cl>O1CCCC1>[C:1]([S:4][CH2:5][C@@H:6]([CH3:10])[C:7](=[O:9])[O:8][C@@H:24]([CH2:28][S:29][CH3:30])[C:25]([OH:27])=[O:26])(=[O:3])[CH3:2]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2724506D-beta-acetylthioisobutyric acidHCID 15647666(R)-2-hydroxy-3-(methylthio)propanoic acid

Produkt 1

HCID 102656742(R)-(3-(Acetylthio)-2(S)-methyl-1-oxopropoxy)-3-(methylthio)propanoic acidAusbeute 15,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

(S)-3-(Acetylthio)-2-methylpropanoic acid (0.38 g, 2.35 mmol) and 1,1'-carbonyldiimidazole (0.38 g, 2.35 mmol) were stirred under nitrogen, in tetrahydrofuran (10 ml). After 30 min, a solution of (R)-2-hydroxy-3-(methylthio)propanoic acid (0.32 g, 2.35 mmol), triethylamine (0.33 ml, 2.35 mmol) and tetrahydrofuran (10 ml) was added dropwise. The reaction mixture was stirred at 25° for 18 h before evaporation of the solvent. The residue was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic extracts were dried (Na2SO4) and the solvent evaporated. Chromatography on silica with dichloromethane/ethyl acetate as eluant gave the sub-title compound (0.1 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d5a2eae0dd0145f8a3bf7310978c8aea
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05348978

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