Dimethylformamide → HCID 57393214, 화합물

HRID 17101

반응식

HRID 17101 반응식
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

참가 물질

9

반응물 6

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acid2회HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1344423-Methoxypropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 57393214HCID 57393214, 화합물

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매2회

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-143b8358ec3a4888b04d3d892bb7d06c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737279B2

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