Tetrahydrofuran → 3-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-6-(phenylethynyl)pyridazine

HRID 46203노트

반응식

HRID 46203 반응식
ClC1N=[N:4][C:5]([CH2:8][C:9]2[CH:14]=[C:13]([C@H:15]3[C@H:20]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C@@H:19]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C@H:18]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[O:16]3)[CH:12]=[CH:11][C:10]=2[Cl:54])=CC=1.C([N:58](CC)[CH:59]([CH3:61])[CH3:60])(C)C.C#[C:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1.O1CCC[CH2:73]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:54][C:10]1[CH:11]=[CH:12][C:13]([C@H:15]2[C@H:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@@H:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:18]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:17]([CH2:45][O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[O:16]2)=[CH:14][C:9]=1[CH2:8][C:5]1[N:4]=[N:58][C:59]([C:60]#[C:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)=[CH:61][CH:73]=1

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 10821PhenylacetyleneHCID 81531DiisopropylethylamineHCID 86664426HCID 86664426, 화합물

생성물 1

HCID 672875763-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-6-(phenylethynyl)pyridazine

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

실험 절차

To a mixture of Intermediate 6 (compound 24, 381 mg, 0.5 mmol), dichlorobis(triphenyl-phosphine)palladium (II) (35 mg, 0.05 mmol) and copper(I) iodide (10 mg, 0.05 mmol) in tetrahydrofuran (10 mL) was added N,N-diisopropylethylamine (0.35 mL, 2.5 mmol) and phenylacethylene (0.07 mL, 0.6 mmol). The resulting mixture was stirred at ambient temperature overnight. After dilution with ethyl acetate, the organic layer was washed with water and brine prior to drying over magnesium sulfate. Filtration through a plug of silica gel and removal of the volatiles under reduced pressure yielded titled compound as a brown solid, which was used without further purification.

후처리

  1. washAfter dilution with ethyl acetate, the organic layer was washed with water and brine
  2. dry with materialto drying over magnesium sulfate
  3. filtrationFiltration
  4. customthrough a plug of silica gel and removal of the volatiles under reduced pressure

출처 및 근거

ORD 기록
ord-7e8229c8b0bc405aafc93935874746f9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541380B2

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