Triethylamine → HCID 22253674, compound

HRID 1064548Notes

Reaction equation

HRID 1064548 reaction equation
[Br:1][CH:2]([CH3:12])[C:3]([NH:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=[O:8])=O.C(N(CC)CC)C.ClC(OCC)=O>CC(C)=O>[Br:1][CH:2]([C:3]1[O:8][C:7](=[O:9])[C:6]([CH3:11])([CH3:10])[N:5]=1)[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22253670HCID 22253670, compound

Product 1

HCID 22253674HCID 22253674, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a stirring mixture of 2-(2-bromopropionylamino)-2-methyl propionic acid (50.00 g, 0.21 mol), triethylamine (23.37 g, 0.23 mol), and 150 mL acetone cooled to 5° C., was added dropwise a solution of ethyl chloroformate (25.07 g, 0.23 mol) in 40 mL acetone. After full addition, the mixture was allowed to warm to room temperature, and was stirred for two hours. The mixture was filtered, and the solid was washed with ether. The solvent was then removed under vacuum, and the residue was filtered. The filtrate was distilled under reduced pressure to give a colorless oil (bp 63-64° C. at 1 mmHg). A yield of 34.73 g (75%) was obtained.

Workup

  1. additionAfter full addition
  2. temperatureto warm to room temperature
  3. filtrationThe mixture was filtered
  4. washthe solid was washed with ether
  5. customThe solvent was then removed under vacuum
  6. filtrationthe residue was filtered
  7. distillationThe filtrate was distilled under reduced pressure
  8. customto give a colorless oil (bp 63-64° C. at 1 mmHg)
  9. customA yield of 34.73 g (75%) was obtained

Sources & evidence

ORD record
ord-553faa2f53c843a2ab11c7c36d64119a
Source dataset
uspto-grants-2005_11
Patent number
US06969749B2

Reaction notes

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