Toluene → HCID 178514666, 화합물

HRID 20907

반응식

HRID 20907 반응식
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]

참가 물질

7

반응물 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

생성물 1

HCID 178514666HCID 178514666, 화합물수율 89%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-d07b1095f64c4a1f966ce0e280cb68d1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745608B2

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