Toluene → HCID 178420607、化合物

HRID 20924

反応式

HRID 20924 の反応式
COC1C=CC(C(C2C=CC(OC)=CC=2)OC(C2C=CC=CC=2)[CH:12]2[CH:16](O)[CH2:15][N:14](C(=O)CCCCC[N:24]3[C:32](=[O:33])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]3=[O:34])[CH2:13]2)=CC=1.C1(C)C=CC=CC=1.C(CC[O:61][P:62]([N:70](C(C)C)C(C)C)N(C(C)C)C(C)C)#N.C(OCC)(=[O:79])C>CCCCCC>[NH:14]1[CH2:15][CH2:16][CH2:12][CH2:13]1.[P:62]([NH2:70])([O-:61])[O:79][N:24]1[C:32](=[O:33])[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=[C:26]2[C:25]1=[O:34]

参加物

6

反応物 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 1317282252-(6-{3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-isoindole-1,3-dione

生成物 1

HCID 178420607HCID 178420607、化合物収率 85%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

実験手順

Compound 77 (1.5 g, 2.26 mmol) was coevaporated with anhydrous toluene (25 mL). To the residue N,N-tetraisopropylammonium tetrazolide (0.127 g, 1.13 mmol) was added and the mixture was dried over P2O5 in a vacuum oven for overnight at 40° C. The reaction mixture was dissolved in acetonitrile/dichloroethane (10 mL) and 2-cyanoethyl-N,N,N′,N′-tetraisopropylphosphorodiamidite (1.362 g, 1.49 mL, 4.52 mmol) was added. The reaction mixture was stirred at ambient temperature for overnight. The completion of the reaction was ascertained by TLC (Rf=0.4 in 1:1 ethyl acetate:hexane). The reaction mixture was concentrated undervacuum and the residue was dissolved in ethyl acetate (100 mL). The organic layer was washed with 5% NaHCO3 (100 mL) and brine (100 mL). The organic layer was dried over anhydrous Na2SO4 filtered and concentrated under reduced pressure. The residue was purified over silica gel (50:49:1, EtOAc:Hexane:triethlyamine) to afford compound 78 as white solid (1.66 g, 85%).

後処理

  1. dry with materialthe mixture was dried over P2O5 in a vacuum oven for overnight at 40° C
  2. dissolutionThe reaction mixture was dissolved in acetonitrile/dichloroethane (10 mL)
  3. concentrationThe reaction mixture was concentrated undervacuum
  4. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  5. washThe organic layer was washed with 5% NaHCO3 (100 mL) and brine (100 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified over silica gel (50:49:1, EtOAc:Hexane:triethlyamine)

出典と根拠

ORDレコード
ord-9aed5765be684fe0a265b91036b54089
出典データセット
uspto-grants-2010_06
特許番号
US07745608B2

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