Methanol → methyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetate

HRID 2366871ノート

反応式

HRID 2366871 の反応式
[CH3:1][CH:2]([O:4][C:5](=[O:23])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[CH:18])[CH:15]=2)[N:10]([C:19](=[O:21])[CH3:20])[C@@H:9]([CH3:22])[CH2:8]1)[CH3:3].CO.[N:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])=[N+:27]=[N-:28]>CN(C)C=O.[Cu]I>[C:19]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[N:28]=[N:27][N:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[CH:18]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:23])[CH2:8][C@@H:9]1[CH3:22])(=[O:21])[CH3:20]

参加物

6

反応物 3

HCID 887MethanolHCID 4020482Methyl 2-azidoacetateHCID 86669236HCID 86669236、化合物

生成物 1

HCID 68185402methyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetate収率 96%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 1-methylethyl[(2S,4R)-1-acetyl-6-ethynyl-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Intermediate 58) (408 mg, 1.298 mmol) in N,N-dimethylformamide (DMF) (8 mL) and methanol (0.9 mL) were successively added methyl azidoacetate (299 mg, 2.60 mmol) and copper(I) iodide (12.36 mg, 0.065 mmol). The resulting mixture was stirred at 100° C. under microwave irradiation for 2 h then cooled to room temperature and partitioned between brine and AcOEt. The layers were separated. The aqueous phase was extracted with EtOAc (3×) and the combined organic layers were washed with brine, dried over a Na2SO4 cartridge and concentrated in vacuo. Purification of the residue on SP4 using a 25 G silica cartridge (gradient: 2 to 10% MeOH in DCM) gave methyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetate (468 mg, 1.046 mmol, 96%) as a viscous yellow oil.

後処理

  1. temperaturethen cooled to room temperature
  2. custompartitioned between brine and AcOEt
  3. customThe layers were separated
  4. extractionThe aqueous phase was extracted with EtOAc (3×)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over a Na2SO4 cartridge
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue on SP4

出典と根拠

ORDレコード
ord-5e58df43176d492e86c69de13b60ef31
出典データセット
uspto-grants-2014_04
特許番号
US08697725B2

反応ノート

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