Triphenylphosphine → 7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61860

반응식

HRID 61860 반응식
[CH3:1][O:2][C:3]1[C:8]2[C:9]([CH3:24])([CH3:23])[C:10]3[NH:11][C:12]4[C:17]([C:18]=3[C:19](=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH:16][CH:15]=[C:14]([C:21]#[N:22])[CH:13]=4.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:44][C:45]1([CH3:52])[O:49][C@H:48](CO)[CH2:47][O:46]1.N(C(OCC)=O)=NC(OCC)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1.C1COCC1>[CH3:44][C:45]1([CH3:52])[O:49][C@H:48]([CH2:1][O:2][C:3]2[C:8]3[C:9]([CH3:24])([CH3:23])[C:10]4[NH:11][C:12]5[C:17]([C:18]=4[C:19](=[O:20])[C:7]=3[CH:6]=[CH:5][CH:4]=2)=[CH:16][CH:15]=[C:14]([C:21]#[N:22])[CH:13]=5)[CH2:47][O:46]1

참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 736056(R)-SolketalHCID 668352707-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

생성물 1

HCID 668345317-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

Under nitrogen atmosphere, 7-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound W3, 15 mg, 0.05 mmol) and triphenylphosphine (40 mg, 3 eq.) were added with THF (1 ml), further added dropwise with ((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (20 mg, 3 eq.) and 2.19 N toluene solution of diethyl azodicarboxylate (68 μL, 3 eq.), and the mixture was stirred at 50° C. for 2 hr. After cooling, the reaction solution was added with ethyl acetate, washed with brine, dried over sodium sulfate, and filtered. The residues obtained after concentration under reduced pressure were purified by preparative TLC (ethyl acetate/dichloromethane), and the resulting solid was washed with dichloromethane to obtain the target compound (brown powder, 5 mg).

후처리

  1. temperatureAfter cooling
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by preparative TLC (ethyl acetate/dichloromethane)
  8. washthe resulting solid was washed with dichloromethane
  9. customto obtain the target compound (brown powder, 5 mg)

출처 및 근거

ORD 기록
ord-4b8e140ba2db4cb3834f3c390b3c7ae3
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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