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

反応式

HRID 17625 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4d95ef807d6142039a3b348d991c8850
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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