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

HRID 356520Notes

Reaction equation

HRID 356520 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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 0.02M 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).

Workup

  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

Sources & evidence

ORD record
ord-78f2165d513047e9b080039205300ffd
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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