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

HRID 926265

반응식

HRID 926265 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f8688558e29c4735b0c40bd716b90d10
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284331B2

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