Triethylamine → HCID 13774519, compound

HRID 495125Notes

Reaction equation

HRID 495125 reaction equation
[NH2:1][C@@H:2]([C:4]([OH:6])=[O:5])[CH3:3].C(N(CC)CC)C.[F:14][C:15]([F:22])([F:21])[C:16](OCC)=[O:17]>CO>[F:14][C:15]([F:22])([F:21])[C:16]([NH:1][C@@H:2]([C:4]([OH:6])=[O:5])[CH3:3])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 71080D-Alanine

Product 1

HCID 13774519HCID 13774519, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the mixture of D-alanine (20.00 g; 0.224 mol) and triethylamine (31.3 ml; 0.224 mol) in absolute methanol (100 ml), ethyl trifluoroacetate (33.4 ml; 0.280 mol) is added and stirred at room temperature to homogenise the mixture (approx. 1 day). The solution is concentrated on a rotavapor (35° C.; 16 mmHg) and then dissolved in the mixture THF/water (1:1; 140 ml). Acidic ion exchanger Dowex 50W-X8 (100 g) is added, stirred for 10 minutes, filtered and concentrated again on a rotavapor (35° C.; 16 mmHg). The residue is sublimed (80° C.; 0.05 mmHg). The pure product in the form of colourless crystals is obtained (33.50 g; 80.8%).

Workup

  1. additionis added
  2. stirringto homogenise the mixture (approx. 1 day)
  3. concentrationThe solution is concentrated on a rotavapor (35° C.; 16 mmHg)
  4. dissolutiondissolved in the mixture THF/water (1:1; 140 ml)
  5. additionAcidic ion exchanger Dowex 50W-X8 (100 g) is added
  6. stirringstirred for 10 minutes
  7. filtrationfiltered
  8. concentrationconcentrated again on a rotavapor (35° C.; 16 mmHg)
  9. custom(80° C.; 0.05 mmHg)
  10. customThe pure product in the form of colourless crystals is obtained (33.50 g; 80.8%)

Sources & evidence

ORD record
ord-be3101733f3f4710a3d4964d4e7edfa7
Source dataset
uspto-grants-2009_05
Patent number
US07538246B2

Reaction notes

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