2,5-Dihydroxybenzoic acid → (2S)-2-methylbutyl 2,5-dihydroxybenzoate

HRID 424307

반응식

HRID 424307 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CS(O[CH2:17][C@@H:18]([CH3:21])[CH2:19][CH3:20])(=O)=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:17][C@@H:18]([CH3:21])[CH2:19][CH3:20])=[O:5]

참가 물질

5

반응물 3

HCID 34692,5-Dihydroxybenzoic acidHCID 516892Sodium BicarbonateHCID 15698189(2S)-2-Methylbutyl methanesulfonate

생성물 1

HCID 59005024(2S)-2-methylbutyl 2,5-dihydroxybenzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
80 °C

실험 절차

To a solution of 2,5-dihydroxybenzoic acid (15.4 g) in DMF (50 ml) DBU (15.3 ml) was drop wise added. After complete addition (10 min) stirring was continued for 30 min at room temperature, then a solution of (2S)-2-methylbutyl methanesulfonate (16.4 g) in DMF (20 ml) was added drop wise. After complete addition (30 min) the reaction mixture was heated to 80° C. for 6 h. It was then cooled to room temperature, poured into saturated solution of NaHCO3 (200 ml) and extracted with ethyl acetate (2×300 ml). The combined extracts were dried over Na2SO4 and evaporated to dryness. The obtained dark oily residue was purified over silica gel column to give nearly pure (2S)-2-methylbutyl 2,5-dihydroxybenzoate as beige oil.

후처리

  1. additionwise added
  2. additionAfter complete addition (10 min)
  3. additionAfter complete addition (30 min) the reaction mixture
  4. temperatureIt was then cooled to room temperature
  5. extractionextracted with ethyl acetate (2×300 ml)
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. customevaporated to dryness
  8. customThe obtained dark oily residue was purified over silica gel column

출처 및 근거

ORD 기록
ord-501a2af4992b46148731bbbee28ad177
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08105662B2

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