Methoxyacetic Acid → N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-2-methoxy-acetamide

HRID 2171040ノート

反応式

HRID 2171040 の反応式
[NH2:1][CH2:2][C:3]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[CH:11][C:10]=2[C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH2:22][C:23]3=[O:28])[CH2:6][O:5][CH2:4]1.[CH3:29][O:30][CH2:31][C:32](O)=[O:33].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1>ClCCl.O.C(N(CC)CC)C>[CH3:16][O:15][C:14]1[C:13]([O:17][CH3:18])=[CH:12][CH:11]=[C:10]([C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH2:22][C:23]3=[O:28])[C:9]=1[O:8][CH2:7][C:3]1([CH2:2][NH:1][C:32](=[O:33])[CH2:31][O:30][CH3:29])[CH2:4][O:5][CH2:6]1

参加物

8

反応物 4

HCID 12251Methoxyacetic AcidHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 674679514-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one

生成物 1

HCID 67467293N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-2-methoxy-acetamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

To a stirring solution of 4-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one (150 mg, 0.391 mmol) in dichloromethane (15 mL), methoxy-acetic acid (142 mg, 1.56 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (112 mg, 0.587 mmol) and 1-Hydroxy-7-azabenzotriazole (HOAt) (106 mg, 0.78 mmol) and triethylamine were added and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined dichloromethane layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-3% methanol in dichloromethane) afforded the title compound as a solid.

後処理

  1. customthe resultant reaction mixture
  2. extractionextracted with dichloromethane (3×)
  3. washThe combined dichloromethane layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography (silica gel, 0-3% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-b03a97b64fd3412ea53728781302fdae
出典データセット
uspto-grants-2015_06
特許番号
US09051290B2

反応ノート

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