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

HRID 356520ノート

反応式

HRID 356520 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-78f2165d513047e9b080039205300ffd
出典データセット
uspto-grants-1998_11
特許番号
US05834506

反応ノート

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