Nitrogen → 2-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-4-nitro-2H-[1,2,3]triazole

HRID 42831ノート

反応式

HRID 42831 の反応式
N#N.[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16]Cl)=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4].[N+:20]([C:23]1[CH:27]=[N:26][NH:25][N:24]=1)([O-:22])=[O:21].CCN(C(C)C)C(C)C>CN(C=O)C.CC(C)=O.CC(=O)OCC.O>[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16][N:25]2[N:24]=[C:23]([N+:20]([O-:22])=[O:21])[CH:27]=[N:26]2)=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4]

参加物

9

反応物 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 668212212-[1-(Tert-butyl-dimethyl-silanyloxy)-ethyl]-5-chloromethyl-oxazole

生成物 1

HCID 673650552-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-4-nitro-2H-[1,2,3]triazole

試薬・触媒・溶媒 4

HCID 180Acetone溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-chloromethyl-oxazole (247 mg, 0.89 mmol) in DMF (1.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (850 mg of a 10% solution in acetone, 0.75 mmol) in DMF (1.0 mL) pre-treated for 30 min with DIPEA (0.26 mL, 1.49 mmol) and the reaction mixture was stirred for 48 h at 50° C. Water (10 mL), followed by EA (20 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over NaSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a yellow oil. TLC:rf (2:1 hept-EA)=0.36. LC-MS-conditions 02: tR=1.11 min; [M+H]+=354.34.

後処理

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (10 mL)
  3. dry with materialextracts were dried over NaSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (2:1 hept-EA)

出典と根拠

ORDレコード
ord-15cead1a2a424cd796dcc89090207190
出典データセット
uspto-grants-2013_09
特許番号
US08536209B2

反応ノート

読み込み中…