Dimethyl Sulfoxide → 1-(4'-{5-[(1-Benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-1-methyl-1H-pyrazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

HRID 919092ノート

反応式

HRID 919092 の反応式
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[N:23][N:24]([CH3:30])[C:25]=4[CH:26]([OH:29])[C:27]#[CH:28])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:31]([N:38]=[N+:39]=[N-:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CS(C)=O.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2].CCOC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[N:23][N:24]([CH3:30])[C:25]=4[CH:26]([C:27]4[N:40]=[N:39][N:38]([CH2:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[CH:28]=4)[OH:29])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

参加物

8

反応物 4

HCID 679Dimethyl Sulfoxide2 回HCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 866970911-{4'-[5-(1-Hydroxy-prop-2-ynyl)-1-methyl-1H-pyrazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

生成物 1

HCID 679596491-(4'-{5-[(1-Benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-1-methyl-1H-pyrazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

試薬・触媒・溶媒 3

HCID 24462Copper Sulfate触媒HCID 962Water溶媒HCID 22728543Water ethylacetate溶媒

実験手順

1-{4′-[5-(1-Hydroxy-prop-2-ynyl)-1-methyl-1H-pyrazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.17 g, 0.45 mmol) and benzyl azide (0.072 g, 0.54 mmol) were combined DMSO (5 mL). Copper(II) sulfate (0.001 g, 0.005 mmol) and sodium ascorbate (0.001 g, 0.05 mmol) were combined in H2O (2 mL) and the solution was added to the DMSO mixture. The reaction was stirred at room temperature for 18 hours then submitted to EtOAc/H2O workup. Purification on silica gel (0-70% EtOAc in hexanes) provided the title compound.

後処理

  1. customPurification on silica gel (0-70% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-b503df4c22b2428b84c04444e54d3af1
出典データセット
uspto-grants-2016_03
特許番号
US09272990B2

反応ノート

読み込み中…