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Dibutyltin oxide → {5-[2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid

HRID 554594
ノート
印刷プレビュー

反応式

HRID 554594 の反応式
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=2[CH2:20][N:21]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]([CH:24]2[CH2:26][CH2:25]2)=[O:23])[CH:11]=1)[CH3:2].C([Sn](=O)CCCC)CCC.[N:45]([Si](C)(C)C)=[N+:46]=[N-:47]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:45]=[N:46][NH:47][N:19]=3)=[CH:14][C:13]=2[CH2:20][N:21]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]([CH:24]2[CH2:26][CH2:25]2)=[O:23])[CH:11]=1)[CH3:2].[CH2:27]([N:21]([CH2:20][C:13]1[CH:14]=[C:15]([C:18]2[N:45]=[N:46][NH:47][N:19]=2)[CH:16]=[CH:17][C:12]=1[C:10]1[CH:11]=[C:6]([CH2:5][C:4]([OH:3])=[O:34])[CH:7]=[N:8][CH:9]=1)[C:22]([CH:24]1[CH2:25][CH2:26]1)=[O:23])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
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

6

反応物 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 67212964(5-{2-[(Benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

生成物 2

HCID 45138332{5-[2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid
HCID 58565080
{5-[2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid ethyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

(5-{2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester (0.253 g, 0.56 mmol) was dissolved in toluene (10 mL). Dibutyltin oxide (0.014 g, 0.06 mmol) was added, followed by azidotrimethylsilane (0.09 mL, 0.67 mmol), and the reaction was stirred at 80° C. for 5 hours, and at 100° C. overnight. The mixture was quenched with H2O and extracted with EtOAc. The combined organic layers were concentrated and purified by preparative HPLC to give {5-[2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid ethyl ester the title compound.

後処理

  1. customat 100° C.
  2. customovernight
  3. customThe mixture was quenched with H2O
  4. extractionextracted with EtOAc
  5. concentrationThe combined organic layers were concentrated
  6. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-1905ee7ed9154e29b9343731b18b9e54
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08049015B2

反応ノート

読み込み中…

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