Dimethylformamide → HCID 57393214、化合物

HRID 17101

反応式

HRID 17101 の反応式
Cl.[CH3:2][N:3]([CH3:12])[CH2:4][CH2:5][CH2:6][N:7]=[C:8]=[N:9][CH2:10]C.O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=N1.C([N:26]([CH:29](C)C)CC)(C)C.[CH3:32][O:33][CH2:34][CH2:35][C:36]([OH:38])=O.[C:39](O)([C:41](F)(F)F)=O.C[N:47](C)C=O>O.CO>[CH3:2][N:3]1[C:4]2=[C:39]3[CH:41]=[C:10]([C:18]4[N:14]=[C:22]([CH2:17][NH:16][C:36](=[O:38])[CH2:35][CH2:34][O:33][CH3:32])[CH:21]=[CH:20][CH:19]=4)[NH:9][C:8]3=[N:7][C:6]([NH:26][CH3:29])=[C:5]2[N:47]=[CH:12]1

参加物

9

反応物 6

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acid2 回HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1344423-Methoxypropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 57393214HCID 57393214、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒2 回

実験手順

To a mixture of A215 (0.020 g, 0.065 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.019 g, 0.098 mmol), 1-hydroxybenzotriazole (0.013 g, 0.098 mmol), and diisopropylethylamine (0.034 mL, 0.195 mmol) in anhydrous dimethylformamide (2 mL) was added 3-methoxypropionic acid (9.20 μL, 0.098 mmol). The reaction mixture was stirred at room temperature overnight (After ˜3 hr, the reaction mixture became homogenous). The solvent was removed under reduced pressure, and the residue was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. Concentration under pressure followed by purification by flash silica gel chromatography using a 5% mixture of methanol in dichloromethane afforded 0.018 g (69%) of A216 as a yellow solid. The compound had an HPLC retention time=1.84 min. (Column: Chromolith SpeedROD 4.6×50 mm—4 min.; Solvent A=10% MeOH, 90% H2O, and 0.1% TFA; Solvent B=90% MeOH, 10% H2O, and 0.1% TFA) and a LC/MS M+1=394.37. 1H NMR (400 MHz, CDCl3) δ ppm 2.62 (t, J=7.15 Hz, 2 H) 3.15 (d, J=6.60 Hz, 3 H) 3.54 (s, 3 H) 3.78 (t, J=7.15 Hz, 2 H) 4.01 (s, 3 H) 4.56 (d, J=6.10 Hz, 2 H) 5.49-5.54 (m, 1 H) 6.96-6.98 (m, 2 H) 7.51-7.58 (m, 3 H) 9.98 (s, 1 H)

後処理

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with dichloromethane
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration under pressure
  6. customfollowed by purification by flash silica gel chromatography
  7. customafforded 0.018 g (69%) of A216 as a yellow solid

出典と根拠

ORDレコード
ord-143b8358ec3a4888b04d3d892bb7d06c
出典データセット
uspto-grants-2010_06
特許番号
US07737279B2

関連ノート

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