tert-Butyl acetate → HCID 66603844, 화합물

HRID 1627910노트

반응식

HRID 1627910 반응식
[I:1][C:2]1[C:7]([CH:8]([OH:13])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:14])[N:5]=[C:4]2[S:15][C:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:3]=12.C(O[C:26]([CH3:29])([CH3:28])[CH3:27])(=O)C.Cl(O)(=O)(=O)=O>>[I:1][C:2]1[C:7]([CH:8]([O:13][C:26]([CH3:29])([CH3:28])[CH3:27])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:14])[N:5]=[C:4]2[S:15][C:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:3]=12

참가 물질

4

반응물 3

HCID 10908tert-Butyl acetateHCID 24247Perchloric AcidHCID 66603698Methyl hydroxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate

생성물 1

HCID 66603844HCID 66603844, 화합물수율 32.6%

실험 절차

To a solution of methyl 2-[4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-hydroxyacetate (2.1 g; 5.03 mmol) in tert-butyl acetate (15 mL; 112 mmol) under a nitrogen atmosphere was added perchloric acid 70% (0.342 mL; 5.52 mmol). The reaction was stirred at room temperature for 3 days and quenched by adding a saturated solution of sodium bicarbonate. The mixture was diluted with dichloromethane and the phases were separated. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethylacetate (1-40%) in heptane furnished 0.776 g (32%) of the title compound as a solid.

후처리

  1. customquenched
  2. additionby adding a saturated solution of sodium bicarbonate
  3. additionThe mixture was diluted with dichloromethane
  4. customthe phases were separated
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash-chromatography on silica gel using a gradient of ethylacetate (1-40%) in heptane

출처 및 근거

ORD 기록
ord-a9fabb154db14636a1c7894625c3781d
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785638B2

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