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

HRID 356520노트

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HRID 356520 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-78f2165d513047e9b080039205300ffd
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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