2-Methyl-2-butanol → Dasabuvir

HRID 58406

반응식

HRID 58406 반응식
C(P(C(C)(C)C)C1C(OC)=CC=C(OC)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)(CC)(C)C.FC(F)(S(O[C:65]1[CH:74]=[CH:73][C:72]2[C:67](=[CH:68][CH:69]=[C:70]([C:75]3[CH:80]=[C:79]([N:81]4[CH:86]=[CH:85][C:84](=[O:87])[NH:83][C:82]4=[O:88])[CH:78]=[C:77]([C:89]([CH3:92])([CH3:91])[CH3:90])[C:76]=3[O:93][CH3:94])[CH:71]=2)[CH:66]=1)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.[CH3:96][S:97]([NH2:100])(=[O:99])=[O:98]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:89]([C:77]1[C:76]([O:93][CH3:94])=[C:75]([C:70]2[CH:71]=[C:72]3[C:67](=[CH:68][CH:69]=2)[CH:66]=[C:65]([NH:100][S:97]([CH3:96])(=[O:99])=[O:98])[CH:74]=[CH:73]3)[CH:80]=[C:79]([N:81]2[CH:86]=[CH:85][C:84](=[O:87])[NH:83][C:82]2=[O:88])[CH:78]=1)([CH3:91])([CH3:90])[CH3:92]

참가 물질

7

반응물 5

HCID 64052-Methyl-2-butanol2회HCID 62657Potassium Phosphate, TribasicHCID 72879MethanesulfonamideHCID 44233348Di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-(1,1'-biphenyl)-2-yl)phosphineHCID 566406691-Butanesulfonic acid, 1,1,2,2,3,3,4,4,4-nonafluoro-, 6-(5-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-3-(1,1-dimethylethyl)-2-methoxyphenyl)-2-naphthalenyl ester

생성물 1

HCID 56640146Dasabuvir

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
80 °C

실험 절차

Tris(dibenzylideneacetone)dipalladium(0) (0.0066 g, 7.16 μmol), di-tert-butyl(2′,4′,6′-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (0.0083 g, 17 μmol) and milled potassium phosphate tribasic (0.334 g, 1.58 mmol) were charged to a 40-mL reaction vial inside an inert atmosphere glove box. t-Amyl alcohol (4 mL) was added, the vial was capped, and the contents were heated to 80° C. and stirred at this temperature for 30 minutes. The reaction mixture was cooled down to the room temperature. 6-(3-tert-Butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (1.0 g, 1.43 mmol), methanesulfonamide (0.163 g, 1.72 mmol) and t-amyl alcohol (8 mL) were added to the 40-mL reaction vial, and the vial was capped. The reaction temperature was raised to 90° C. and the contents were stirred for 5 hours. HPLC analysis of the reaction mixture showed that the product was formed in 94 area % at 210 nm.

후처리

  1. additionwere charged to a 40-mL reaction vial inside an inert atmosphere glove box
  2. customthe vial was capped
  3. temperatureThe reaction mixture was cooled down to the room temperature
  4. customthe vial was capped
  5. temperatureThe reaction temperature was raised to 90° C.
  6. stirringthe contents were stirred for 5 hours
  7. customwas formed in 94 area % at 210 nm

출처 및 근거

ORD 기록
ord-dfb4cd3bda804dacb31b92974c6d4431
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434698B2

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