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Cesium carbonate → (r/s)-3-(Tert-butoxycarbonylamino)-1-[4-(tert-butoxycarbonylamino)-5-isoquinolinesulfonyl]pyrrolidine

HRID 1436029
ノート
印刷プレビュー

反応式

HRID 1436029 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19](Br)=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:74](=[O:81])([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])[NH2:75].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([NH:75][C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:81])=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 634876Binap, (A+-)-HCID 67242856(r/s)-3-(Tert-butoxycarbonylamino)-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine

生成物 1

HCID 67243815(r/s)-3-(Tert-butoxycarbonylamino)-1-[4-(tert-butoxycarbonylamino)-5-isoquinolinesulfonyl]pyrrolidine収率 32.5%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A suspension of Intermediate 1 (137 mg) obtained in Example 1, Step A, tris(dibenzylideneacetone)dipalladium(0) (55 mg, Aldrich), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (37 mg, Aldrich), tert-butyl carbamate (70 mg, Aldrich), and cesium carbonate (196 mg, Aldrich) in toluene (5 ml) is stirred at 100° C. for 15 hours. The reaction mixture is cooled to room temperature, and then added with ethyl acetate (5 ml), and the insoluble matters are removed by filtration through Celite. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (48 mg (predictive yield)).

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe insoluble matters are removed by filtration through Celite
  3. customThe solvent is evaporated under reduced pressure
  4. customthe residue is purified by silica gel chromatography (n-hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-7d270ce7352342e3bbb64b8723136af7
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07618984B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート