Triethylamine → HCID 22253674, compound

HRID 226196Notes

Reaction equation

HRID 226196 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-f1583da24e854b89b45dd0f389a50517
Source dataset
uspto-grants-2009_07
Patent number
US07557177B2

Reaction notes

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