Tributyltin azide → cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl 3-(1H-tetrazol-5-yl)benzoate

HRID 858196ノート

反応式

HRID 858196 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=1)[C:6]([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])[CH2:10]1)=[O:7])#[N:2].C([Sn]([N:46]=[N+:47]=[N-:48])(CCCC)CCCC)CCC>C1(C)C(C)=CC=CC=1>[NH:46]1[C:1]([C:3]2[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=2)[C:6]([O:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][CH2:16][C:17]3[N:18]=[C:19]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)[O:20][C:21]=3[CH3:22])[CH2:10]2)=[O:7])=[N:2][N:48]=[N:47]1

参加物

4

反応物 2

HCID 4984872Tributyltin azideHCID 69655148cis-3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl 3-cyanobenzoate

生成物 1

HCID 178434850cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl 3-(1H-tetrazol-5-yl)benzoate

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
160 °C

実験手順

0.06 g of cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl 3-cyanobenzoate is dissolved in 5 ml of xylene, 150 μm of tributyltin azide are added and the mixture is heated under reflux at 160° C. for 24 hours. The reaction is terminated by addition of 1 ml of trifluoroacetic acid (in 1 ml of methanol), 3 ml of water are added and the mixture is extracted with ethyl acetate (2×10 ml). The combined organic phases are washed with saturated sodium chloride solution and dried over magnesium sulfate, and the solvent is then removed under reduced pressure. Purification by preparative HPLC gives 0.04 g of the desired cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl 3-(1H-tetrazol-5-yl)benzoate as an amorphous solid.

後処理

  1. temperaturethe mixture is heated
  2. customThe reaction is terminated by addition of 1 ml of trifluoroacetic acid (in 1 ml of methanol), 3 ml of water
  3. additionare added
  4. extractionthe mixture is extracted with ethyl acetate (2×10 ml)
  5. washThe combined organic phases are washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent is then removed under reduced pressure
  8. customPurification by preparative HPLC

出典と根拠

ORDレコード
ord-5ee19fe33fe84d0f8f2e0bbb7f8c5439
出典データセット
uspto-grants-2006_12
特許番号
US07148246B2

反応ノート

読み込み中…