Diisopropylethylamine → Tert-butyl(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethoxycarbonylamino)acetate

HRID 856178ノート

反応式

HRID 856178 の反応式
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)C(C)C)(C)C.ClC(Cl)(O[C:24](=[O:30])[O:25][C:26](Cl)(Cl)Cl)Cl.O[CH2:33][C:34]1(C)[O:38][C:37]2=[N:39][C:40]([N+:42]([O-:44])=[O:43])=[CH:41][N:36]2[CH2:35]1>C(Cl)Cl.CN(C=O)C.O>[C:2]([O:6][C:7](=[O:10])[CH2:8][NH:9][C:24]([O:25][CH2:26][C:34]1([CH3:33])[O:38][C:37]2=[N:39][C:40]([N+:42]([O-:44])=[O:43])=[CH:41][N:36]2[CH2:35]1)=[O:30])([CH3:5])([CH3:4])[CH3:3]

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 23081240(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methanol

生成物 1

HCID 69481489Tert-butyl(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethoxycarbonylamino)acetate収率 14.8%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Glycine tert-butyl ester monohydrochloride (0.52 g, 2.27 mmol) in methylene chloride (5 ml) and N,N-diisopropylethylamine (1.05 ml, 4.53 mmol) were added to a triphosgene (0.30 g, 0.76 mmol) in methylene chloride (10 ml) with cooling on ice-bath followed by stirring at room temperature for 2 hours. Insoluble matters were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was added to a solution of 2-hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 33 (0.30 g, 1.51 mmol) in DMF (3 ml) with cooling on ice-bath. Then cuprous chloride (75 mg, 0.76 mmol) was added to the resulting mixture followed by stirring at room temperature for 22 hours. Water was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/2) to afford tert-butyl(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethoxycarbonylamino)acetate (40 mg, yield 7%) as a white solid.

後処理

  1. temperaturewith cooling on ice-bath
  2. customInsoluble matters were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. temperaturewith cooling on ice-bath
  5. stirringby stirring at room temperature for 22 hours
  6. extractionthe resulting mixture was extracted with ethyl acetate
  7. washThe organic phase was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/2)

出典と根拠

ORDレコード
ord-4747b51ce04845eb904ea8dd8931ba12
出典データセット
uspto-grants-2007_08
特許番号
US07262212B2

反応ノート

読み込み中…