Triethylamine → Methyl 3-((2-iodophenethyl)amino)-2-methyl-3-oxopropanoate

HRID 926265

反応式

HRID 926265 の反応式
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[I:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH2:27][NH2:28].[CH3:29][O:30][C:31](=[O:37])[CH:32]([CH3:36])[C:33](O)=[O:34].CCN(CC)CC.[OH-].[Na+]>CCOC(C)=O>[I:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH2:27][NH:28][C:33](=[O:34])[CH:32]([CH3:36])[C:31]([O:30][CH3:29])=[O:37]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 111923Propylphosphonic anhydrideHCID 3006933-Methoxy-2-methyl-3-oxopropanoic acidHCID 105146162-(2-Iodophenyl)ethanamine

生成物 1

HCID 86711343Methyl 3-((2-iodophenethyl)amino)-2-methyl-3-oxopropanoate収率 78.5%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

A solution of T3P in AcOEt (50%, 26.2 mL, 44.0 mmol) was added dropwise at 0° C. under N2 to a clear solution of 2-(2-iodophenyl)ethanamine (9.45 g, 38.2 mmol), 3-methoxy-2-methyl-3-oxopropanoic acid (5.05 g, 38.2 mmol) and Et3N (10.7 mL, 76.0 mmol) in AcOEt (350 mL). The mixture was stirred at RT for 6 days. A 2N aqueous solution of NaOH (50 mL) was then added to the reaction and the mixture was extracted with AcOEt. The combined org. layers were then dried over Na2SO4, filtered and concentrated in vacuo. The yellow oil obtained was purified by flash chromatography (SiO2, cHEx/AcOEt 100:0 to 50:50) to afford the title compound (10.83 g) as a clear oil. UPLC-MS: MS 362.2 (M+H+); UPLC rt 0.95 min.

後処理

  1. extractionthe mixture was extracted with AcOEt
  2. dry with materiallayers were then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe yellow oil obtained
  6. customwas purified by flash chromatography (SiO2

出典と根拠

ORDレコード
ord-f8688558e29c4735b0c40bd716b90d10
出典データセット
uspto-grants-2016_03
特許番号
US09284331B2

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