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

HRID 865465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 865465
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 AcidAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 260Hydrogen BromideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Glacial HOAc (120 ml) was added to a suspension of the product of step 8 (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 6h and at 50° overnight. The reaction mixture was then cooled to r.t., 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 aq 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 17.6 g of the title compound as a pale yellow liquid which was used as such for the next step.

Aufarbeitung

  1. dissolutionthe dissolution
  2. extractionextracted with CH2Cl2 (7×)
  3. concentrationThe combined organic extracts were concentrated in vacuo
  4. additionThe residue was diluted with toluene (500 mL)
  5. concentrationconcentrated in vacuo 5 times
  6. customto remove HOAc
  7. dissolutionThe residue was dissolved in 1M aq KOH (750 mL)
  8. washwashed with CH2Cl2 (4×)
  9. extractionextracted with CH2Cl2 (6×)
  10. dry with materialThe combined organic extracts were dried over Na2SO4
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-19fb5ecaeac7493f99684ceaf399c700
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565473

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