Oxamic Acid → N-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethyl]oxamide

HRID 275490

反応式

HRID 275490 の反応式
[C:1]([OH:6])(=O)[C:2]([NH2:4])=[O:3].CN1CCOCC1.ClC(OCC)=O.[CH:20]1([O:25][C:26]2[CH:27]=[C:28]([CH2:34][CH2:35][NH2:36])[CH:29]=[CH:30][C:31]=2[O:32][CH3:33])[CH2:24][CH2:23][CH2:22][CH2:21]1.[Cl-].[NH4+]>COCCOC>[CH:20]1([O:25][C:26]2[CH:27]=[C:28]([CH2:34][CH2:35][NH:36][C:1]([C:2]([NH2:4])=[O:3])=[O:6])[CH:29]=[CH:30][C:31]=2[O:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH2:24]1

参加物

7

反応物 5

HCID 974Oxamic AcidHCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 112763943-Cyclopentyloxy-4-methoxyphenethylamine

生成物 1

HCID 9861348N-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethyl]oxamide収率 30%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

To a suspension of oxamic acid (1.76 g, 20 mmol) in 1,2-dimethoxyethane (75 mL) under an argon atmosphere was added dropwise N-methylmorpholine (2.55 mL, 23 mmol) followed by ethyl chloroformate (2.20 mL, 23 mmol). After stirring for 1 h at room temperature, a solution of 2-(3-cyclopentyloxy-4-methoxy-phenyl)ethylamine (4.65 g, 20 mmol) in 1,2-dimethoxyethane (30 mL) was added over 5 min, and the resulting mixture was stirred for 2 h. Saturated aqueous ammonium chloride was added and the solvent was removed under reduced pressure. The solid residue was dissolved in methanol/methylene chloride, washed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 1% i-propanol/methylene chloride to provide the oxamide (1.82 g, 30%): m.p. 175°-175.5° C.

後処理

  1. stirringthe resulting mixture was stirred for 2 h
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe solid residue was dissolved in methanol/methylene chloride
  4. washwashed successively with water, 10% hydrochloric acid, aqueous sodium bicarbonate and water
  5. dry with materialdried (potassium carbonate)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with 1% i-propanol/methylene chloride

出典と根拠

ORDレコード
ord-11799f87b34444998fe8615eefb7b91c
出典データセット
uspto-grants-1995_02
特許番号
US05393788

関連ノート

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