Toluene → HCID 178514666、化合物

HRID 1055787

反応式

HRID 1055787 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-3a8b045f6da349cbaf2a25c5ddf8708f
出典データセット
uspto-grants-2016_07
特許番号
US09394540B2

関連ノート

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