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Anisole → HCID 58155274, 화합물

HRID 1929493
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HRID 1929493 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]2([CH3:26])[N:13](CC3C=CC(OC)=CC=3)[C:12](=[O:23])[C:11]([CH3:25])([CH3:24])[O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C1(OC)C=CC=CC=1.FC(F)(F)S(O)(=O)=O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]2([CH3:26])[NH:13][C:12](=[O:23])[C:11]([CH3:25])([CH3:24])[O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7519AnisoleHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 58155245HCID 58155245, 화합물

생성물 1

HCID 58155274HCID 58155274, 화합물

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

반응 조건

온도
73 °C

실험 절차

A solution of (R)-5-(3-bromo-phenyl)-4-(4-methoxy-benzyl)-2,2,5-trimethyl-morpholin-3-one (487 mg, 1.2 mmol) and anisole (2.305 g, 21.3 mmol) in trifluoroacetic acid (6 ml) was treated dropwise with trifluoromethanesulfonic acid (1.19 ml). After complete addition, the violet reaction mixture was heated at 73° C. for 23 hours. The cooled reaction mixture was poured into a saturated solution of sodium hydrogen-carbonate which was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated at reduced pressure. The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 66/34 as the eluent. The product containing fractions (550 mg, orange foam) were collected and engaged in the next step without further purification and characterization.

후처리

  1. additionAfter complete addition
  2. customThe cooled reaction mixture
  3. extractionwas extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated at reduced pressure
  8. customThe crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 66/34 as the eluent
  9. additionThe product containing fractions (550 mg, orange foam)
  10. customwere collected
  11. customengaged in the next step without further purification and characterization

출처 및 근거

ORD 기록
ord-f6d0572062204153ab894cd56e1f092f
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08188079B2

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