Ethyl (2-((2-hydroxypropyl)amino)-2-oxoacetyl)glycinate → Ethyl (2-oxo-2-((2-oxopropyl)amino)acetyl)glycinate

HRID 1016258

反応式

HRID 1016258 の反応式
[CH2:1]([O:3][C:4]([CH2:6][NH:7][C:8]([C:10]([NH:12][CH2:13][CH:14]([OH:16])[CH3:15])=[O:11])=[O:9])=[O:5])[CH3:2].Br([O-])(=O)=O.[Na+]>O.C(OCC)(=O)C.[Cl-].[Na+].O.O.[Ru](Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([CH2:6][NH:7][C:8]([C:10]([NH:12][CH2:13][C:14](=[O:16])[CH3:15])=[O:11])=[O:9])=[O:5])[CH3:2]

参加物

7

反応物 2

HCID 10537524Ethyl (2-((2-hydroxypropyl)amino)-2-oxoacetyl)glycinateHCID 23668195Sodium Bromate

生成物 1

HCID 10823329Ethyl (2-oxo-2-((2-oxopropyl)amino)acetyl)glycinate収率 92%

試薬・触媒・溶媒 4

HCID 6093376Ruthenium trichloride hydrate触媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a stirred solution of N-(ethoxycarbonyl-methyl)-N′-(2-hydroxy-1-propyl)oxamide (8.0 g, 34.5 mmol), as prepared in the preceding step, in water (50 mL) under nitrogen at 50° C. was added ruthenium (III) chloride hydrate (75 mg, 0.35 mmol). The reaction flask was removed from the heating bath, and a solution of sodium bromate (5.2 g, 34.5 mmol) in water (40 mL) was added dropwise. The reaction mixture was allowed to cool to room temperature, and then diluted with ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate (2×), then saturated with sodium chloride and extracted again (×2). The combined ethyl acetate layers were washed with brine, dried over Na2SO4, and treated with activated carbon. Evaporation of the solvent and drying under high vacuum provided the title compound as a white solid (7.3 g, 92%). 1H NMR (400 MHz, CDCl3) δ 7.99 (s(br), 1H), 7.84 (s(br), 1H), 4.24 (q, 2H, J=7.1 Hz), 4.19 (d, 2H, J=5.2 Hz), 4.10 (d, 2H, J=5.7 Hz), 2.24 (s, 3H), 1.30 (t, 3H, J=7.1 Hz).

後処理

  1. customThe reaction flask was removed from the heating bath
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  3. extractionsaturated with sodium chloride and extracted again (×2)
  4. washThe combined ethyl acetate layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. additiontreated with activated carbon
  7. customEvaporation of the solvent
  8. customdrying under high vacuum

出典と根拠

ORDレコード
ord-05a75e7048db4cf9b4b258b7cef0d25f
出典データセット
uspto-grants-2002_11
特許番号
US06476016B2

関連ノート

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