Triethylamine → HCID 86594426, compound

HRID 2112202Notes

Reaction equation

HRID 2112202 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6]I.[CH3:17][O:18][CH2:19][CH2:20][NH:21][CH3:22].C(N(CC)CC)C>O1CCOCC1>[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6][N:21]([CH2:20][CH2:19][O:18][CH3:17])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 300977(2-Methoxyethyl)(methyl)amineHCID 14394150Methyl (S)-2-(Boc-amino)-4-iodobutanoate

Product 1

HCID 86594426HCID 86594426, compoundYield 492.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (S)-2-tert-butoxycarbonylamino-4-iodobutyric acid methyl ester (0.200 g, 0.58 mmol), (2-methoxyethyl)-methylamine (0.062 g, 0.70 mmol), and triethylamine (0.41 mL, 2.9 mmol) in dioxane (1 mL) was stirred at 70° C. for 16 hours. The mixture was cooled to room temperature, concentrated under reduced pressure, and dissolved in dichloromethane (20 mL). The solution was washed with water (3×10 mL), brine (10 mL), dried over MgSO4, filtered through Celite, and concentrated under reduced pressure. The tan oil was chromatographed eluting with ether to provide 0.87 g of pale yellow oil (49% yield).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutiondissolved in dichloromethane (20 mL)
  4. washThe solution was washed with water (3×10 mL), brine (10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered through Celite
  7. concentrationconcentrated under reduced pressure
  8. customThe tan oil was chromatographed
  9. washeluting with ether

Sources & evidence

ORD record
ord-5b95a39dda4e4d7693709aea2ce7b1eb
Source dataset
uspto-grants-2009_04
Patent number
US07521447B2

Reaction notes

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