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

HRID 532892

Reaction equation

HRID 532892 reaction equation
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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c313aadacd8f46eb9bbfcda15f98a713
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Linked notes

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