2-Azidoethanol → 1-methylethyl {(2S,4R)-1-acetyl-6-[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

HRID 2366937ノート

反応式

HRID 2366937 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].[N:24]([CH2:27][CH2:28][OH:29])=[N+:25]=[N-:26]>CN(C)C=O.CO.[Cu]I>[C:19]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[N:26]=[N:25][N:24]([CH2:27][CH2:28][OH:29])[CH:18]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:23])[O:4][CH:2]([CH3:1])[CH3:3])[CH2:8][C@@H:9]1[CH3:22])(=[O:21])[CH3:20]

参加物

6

反応物 2

HCID 1231182-AzidoethanolHCID 86669236HCID 86669236、化合物

生成物 1

HCID 529354541-methylethyl {(2S,4R)-1-acetyl-6-[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate収率 62%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 887Methanol溶媒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) (100 mg, 0.318 mmol) in a mixture of N,N-dimethylformamide (DMF) (1.8 mL) and methanol (0.200 mL) were successively added 2-azidoethanol (55.4 mg, 0.636 mmol) and copper(I) iodide (3.03 mg, 0.016 mmol). The resulting mixture was stirred at 100° C. under microwave irradiation for 2 h then cooled to room temperature. The reaction mixture was partitioned between EtOAc and brine and 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 10 G silica cartridge (gradient: 2 to 10% MeOH in DCM) gave 1-methylethyl {(2S,4R)-1-acetyl-6-[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (83 mg, 0.198 mmol, 62%) as an off white solid.

後処理

  1. temperaturethen cooled to room temperature
  2. customThe reaction mixture was partitioned between EtOAc and brine
  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-2f35e861ce644e2aaececd6bfc4dce47
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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