Acetic Acid → 2-(S)-(Phenylmethylthiomethyl)butanoic Acid

HRID 1590098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590098
CC(O)=O.[C:5]1([CH2:11][S:12][CH2:13][C@@H:14]([CH2:25][CH3:26])[C:15]([O:17]CC2C=CC=CC=2)=[O:16])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>Br.O>[C:5]1([CH2:11][S:12][CH2:13][C@@H:14]([CH2:25][CH3:26])[C:15]([OH:17])=[O:16])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 2

HCID 176Acetic Acid2×HCID 9995793Benzyl 2-(S)-(Phenylmethylthiomethyl)butanoate

Produkt 1

HCID 102630532-(S)-(Phenylmethylthiomethyl)butanoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 260Hydrogen BromideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Glacial HOAc (120 mL) was added to a suspension of the product of Step 4 (32.4 g, approx. 103 mmol) in 210 mL of 30-32% anhydrous HBr in glacial HOAc (approx. 1.03 mol) to complete the dissolution. The resulting solution was stirred at 70° C. for 6 hours and at 50° overnight. The reaction mixture was then cooled to room temperature, diluted with H2O (750 mL) and extracted with CH2Cl2 (7×). The combined organic extracts were concentrated in vacuo. The residue was diluted with toluene (500 mL) and concentrated in vacuo 5 times to remove HOAc. The residue was dissolved in 1M aqueous KOH (750 mL), washed with CH2Cl2 (4×), acidified to pH 1 with concentrated HCl and extracted with CH2Cl2 (6×). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to afford a pale yellow liquid which was used as such for the next step. 1H NMR (CDCl3): δ0.91 (3H, t), 1.66 (2H, m), 2.44-2.56 (2H, m), 2.65-2.75 (1H, m), 3.73 (2H, s), 7.31 (5H, br s).

Aufarbeitung

  1. dissolutionthe dissolution
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. extractionextracted with CH2Cl2 (7×)
  4. concentrationThe combined organic extracts were concentrated in vacuo
  5. additionThe residue was diluted with toluene (500 mL)
  6. concentrationconcentrated in vacuo 5 times
  7. customto remove HOAc
  8. dissolutionThe residue was dissolved in 1M aqueous KOH (750 mL)
  9. washwashed with CH2Cl2 (4×)
  10. extractionextracted with CH2Cl2 (6×)
  11. dry with materialThe combined organic extracts were dried over Na2SO4
  12. concentrationconcentrated in vacuo
  13. customto afford a pale yellow liquid which

Quellen und Nachweise

ORD-Eintrag
ord-a67192b3d28b426e99eee8fce639e6d3
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05202321

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