Chloroacetyl chloride → (S)-2-chloro-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamide

HRID 1043535ノート

反応式

HRID 1043535 の反応式
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH:9]([NH2:13])[CH2:8][O:7]2)([O-:3])=[O:2].C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:21][CH2:22][C:23]([NH:13][C@@H:9]1[CH2:8][O:7][C:6]2=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][N:11]2[CH2:10]1)=[O:24]

参加物

6

反応物 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 598406212-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-amine

生成物 1

HCID 68207026(S)-2-chloro-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamide収率 50%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Under argon protection, I-7-(S)-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine-6-amine (134 mg, 0.73 mmol) was dissolved in anhydrous DMF (2 mL), added triethylamine (0.3 mL, 2.18 mmol), added dropwise chloroacetyl chloride (0.082 mL, 1.09 mmol) at 0° C., stirred for 2 h at room temperature, added saturated sodium bicarbonate solution, extracted by ethyl acetate, followed by anhydrous sodium sulphate drying and suction filtration, spun dry solvents, separated by column chromatography to give 92 mg yellow viscous liquid, yield was 50%.

後処理

  1. extractionextracted by ethyl acetate
  2. filtrationfollowed by anhydrous sodium sulphate drying and suction filtration
  3. customseparated by column chromatography

出典と根拠

ORDレコード
ord-759d236d1fb04006b6fba195e4017cd1
出典データセット
uspto-grants-2013_10
特許番号
US08563547B2

反応ノート

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