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Triethylamine → HCID 22253674, compound

HRID 1072694
Notes
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Reaction equation

HRID 1072694 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22253670HCID 22253670, compound

Product 1

HCID 22253674HCID 22253674, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirring mixture of 2-(2-bromo-propionylamino)-2-methyl-propionic acid (50.0 g; 0.21 mol), triethylamine (23.37 g; 0.23 mol) and 150 mL acetone, cooled with an ice bath, was added a solution of ethyl chloroformate (25.07 g; 0.23 mol) in 40 mL acetone over a period of 10 minutes. The reaction mixture was then allowed to warm to room temperature and was stirred for 2 hours. The mixture was then filtered, and the solid was washed with 150 mL ether. The combined filtrate was concentrated under vacuum. Ether (100 mL) was added to the residue, and the mixture was filtered. After removal of the solvent under vacuum, the filtrate residue was distilled under reduced pressure (63-64° C.; 1 mmHg) to give 34.73 g (75%) of a colorless oil.

Workup

  1. temperaturecooled with an ice bath
  2. filtrationThe mixture was then filtered
  3. washthe solid was washed with 150 mL ether
  4. concentrationThe combined filtrate was concentrated under vacuum
  5. additionEther (100 mL) was added to the residue
  6. filtrationthe mixture was filtered
  7. customAfter removal of the solvent under vacuum
  8. distillationthe filtrate residue was distilled under reduced pressure (63-64° C.; 1 mmHg)

Sources & evidence

ORD record
ord-13d0d55dd77045089dbb6100dd87cf67
Source dataset
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06911510B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes