Tributyltin azide → HCID 178521906、化合物

HRID 133700

反応式

HRID 133700 の反応式
C([Sn]([N:14]=[N+:15]=[N-:16])(CCCC)CCCC)CCC.[CH2:17]([O:24][C:25]1[CH:26]=[C:27]([CH:39]=[C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:41]=1)[C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][N:32]=1)=[O:29])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH2:43]([O:42][C:40]1[CH:39]=[C:27]([CH:26]=[C:25]([O:24][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:41]=1)[C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[NH:16][N:15]=[N:14][N:38]=2)=[CH:33][N:32]=1)=[O:29])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

参加物

4

反応物 2

HCID 4984872Tributyltin azideHCID 230729493,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide

生成物 1

HCID 178521906HCID 178521906、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Tributyltin azide (156 μL, 0.57 mmol) was added to a suspension of 3,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide (180 mg, 0.41 mmol) in toluene (3 mL). The mixture was heated at reflux for 16 hours. The suspension was cooled and partitioned between ethyl acetate and hydrochloric acid (1M). The organic layer was concentrated in vacuo and the residue was purified by MPLC on silica MPLC (eluting with 1% methanol/DCM to 15% methanol/DCM). The tetrazole was obtained as a colourless solid (113 mg, 57%). 1H NMR δ (d6-DMSO): 5.19 (4H, s); 6.88 (1H, s); 7.26-7.48 (12H, m); 8.40 (1H, d); 8.46 (1H, dd); 9.04 (1H, s); 11.13 (1H, br s); m/z (LCMS; ESI+) 479 (MH+).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe suspension was cooled
  4. custompartitioned between ethyl acetate and hydrochloric acid (1M)
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was purified by MPLC on silica MPLC (eluting with 1% methanol/DCM to 15% methanol/DCM)

出典と根拠

ORDレコード
ord-5cc050a25abf4deb850b771018e040a0
出典データセット
uspto-grants-2008_06
特許番号
US07390908B2

関連ノート

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