Toluene → HCID 178514666、化合物

HRID 20907

反応式

HRID 20907 の反応式
COC1C=CC(C(C2C=CC(OC)=CC=2)[O:10][CH:11](C2C=CC=CC=2)[CH:12]2[CH2:16][CH:15]([OH:17])[CH2:14][N:13]2C(=O)CCCCC[N:24]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]2=[O:34])=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>ClCCl.CCCCCC>[OH:17][CH:15]1[CH2:14][NH:13][C@H:12]([CH2:11][OH:10])[CH2:16]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

7

反応物 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 1317282162-(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-isoindole-1,3-dione

生成物 1

HCID 178514666HCID 178514666、化合物収率 89%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

Compound 44a (9.0 g, 13.57 mmol) was coevaporated with anhydrous toluene (50 mL). To the residue N,N-tetraisopropylammonium tetrazolide (0.766 g, 6.8 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 dichloromethane (20 mL) and 2-cyanoethyl-N,N,N′,N′-tetraisopropylphosphorodiamidite (6.13 g, 6.7 mL, 20.35 mmol) was added. The reaction mixture was stirred at ambient temperature for overnight. The completion of the reaction was ascertained by TLC (Rf=0.7 in 1:1 ethyl acetate:hexane). The reaction mixture was diluted with dichloromethane (100 mL) and 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 45a as white solid (10.5 g, 89%).

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 dichloromethane (20 mL)
  3. washwashed with 5% NaHCO3 (100 mL) and brine (100 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified over silica gel (50:49:1, EtOAc:Hexane:triethlyamine)

出典と根拠

ORDレコード
ord-d07b1095f64c4a1f966ce0e280cb68d1
出典データセット
uspto-grants-2010_06
特許番号
US07745608B2

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