2,6-Di-tert-butyl-4-methylphenol → tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate

HRID 17625

반응식

HRID 17625 반응식
Br[C:2]1[C:10]2[O:9][C:8]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[N:7][C:6]=2[C:5]([C:16]#[N:17])=[C:4]([CH3:18])[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C[N:26](C1CCC([Sn](CCCC)(CCCC)CCCC)=C1)[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].C([C:56]1[C:61](O)=[C:60]([C:63]([CH3:66])([CH3:65])C)C=C(C)C=1)(C)(C)C>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:16]([C:5]1[C:6]2[N:7]=[C:8]([C:11](=[O:12])[N:13]([CH3:15])[CH3:14])[O:9][C:10]=2[C:2]([C:56]2[CH2:61][CH2:60][CH:63]([CH2:65][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:66]=2)=[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4]=1[CH3:18])#[N:17]

참가 물질

6

반응물 3

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 68584969tert-Butyl methyl-(3-tri-n-butylstannylcyclopent-2-enyl)carbamateHCID 685851757-bromo-4-cyano-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

생성물 1

HCID 86630887tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate수율 88%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

7-Bromo-4-cyano-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-339) (275 mg, 0.72 mmol) and tert-butyl methyl-(3-tri-n-butylstannylcyclopent-2-enyl)carbamate (I-332) (453 mg, 0.93 mol) were dissolved in 1,4-dioxane (8 ml), and at room temperature, 2,6-di-tert-butyl-paracresol (3 mg, 0.01 mmol) and then bis(triphenylphosphine)palladium(II) dichloride (50 mg, 0.07 mmol) were added. The solution was stirred under nitrogen atmosphere at 100° C. for 24 hours, then cooled to room temperature. The insoluble matter was separated by filtration with washing with ethyl acetate. The filtrate was concentrated under reduced pressure. The solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=2:1, v/v) to obtain the entitled compound (316 mg, 88%) as a colorless gel.

후처리

  1. temperaturecooled to room temperature
  2. customThe insoluble matter was separated by filtration
  3. washwith washing with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe solvent was evaporated away
  6. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

출처 및 근거

ORD 기록
ord-4d95ef807d6142039a3b348d991c8850
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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