D-1,4-Dithiothreitol → (5-tert-Butyl-4-mercapto-2-methyl-phenoxy)acetic acid methyl ester

HRID 1003876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003876
[CH3:1][O:2][C:3](=[O:20])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:9]([S:16]C#N)=[CH:8][C:7]=1[CH3:19].SC[C@H]([C@@H](CS)O)O>CCO>[CH3:1][O:2][C:3](=[O:20])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:9]([SH:16])=[CH:8][C:7]=1[CH3:19]

Komponenten

4

Edukt 2

HCID 446094D-1,4-DithiothreitolHCID 54333600(5-Tert-butyl-2-methyl-4-thiocyanato-phenoxy)acetic acid methyl ester

Produkt 1

HCID 54427811(5-tert-Butyl-4-mercapto-2-methyl-phenoxy)acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1.00 g (3.4 mmol) of (5-tert-butyl-2-methyl-4-thiocyanato-phenoxy)acetic acid methyl ester prepared in Example KKK was combined with 3.16 g (20 mmol) dithiothreitol (DTT) in a solution of 10 mL 0.02 M K2PO4 buffer and 40 mL of EtOH. The reaction was refluxed overnight, then cooled and partially concentrated. After dilution with water, the mixture was extracted with EtOAc, and the organic layer washed with saturated aqueous brine, dried (Na2SO4) and concentrated. The residue was chromatographed on silica gel eluting with 3:1 hexanes:EtOAc, to give the title compound. 1H NMR (CDCl3) δ 1.44 (s, 9 H), 2.19 (s, 3 H), 3.46 (s, 1 H), 3.80 (s, 3 H), 4.62 (s, 2 H), 6.76 (s, 1 H), 7.06 (s, 1 H).

Aufarbeitung

  1. temperatureThe reaction was refluxed overnight
  2. temperaturecooled
  3. concentrationpartially concentrated
  4. extractionAfter dilution with water, the mixture was extracted with EtOAc
  5. washthe organic layer washed with saturated aqueous brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with 3:1 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-08f0dc64142c47b081b837ce5de682e9
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046355

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