Tributyltin azide → HCID 178521906, 화합물

HRID 133700

반응식

HRID 133700 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 178521906HCID 178521906, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-5cc050a25abf4deb850b771018e040a0
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390908B2

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