Triethylamine → HCID 22253673, compound

HRID 1593218Notes

Reaction equation

HRID 1593218 reaction equation
ClC(OCC)=O.[Br:7][C:8]([CH3:19])([CH3:18])[C:9]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14])=O.C(N(CC)CC)C>CC(C)=O>[Br:7][C:8]([C:9]1[O:14][C:13](=[O:15])[C:12]([CH3:17])([CH3:16])[N:11]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22253669HCID 22253669, compound

Product 1

HCID 22253673HCID 22253673, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of ethyl chloroformate (32.4 g, 0.30 mol) in 50 mL acetone was added dropwise to a stirring mixture of 2-(2-bromo-2-methyl propionylamino)-2-methylpropionic acid (67.9 g, 0.27 mol) and triethylamine (30.0 g, 0.30 mol) in 200 mL of acetone at −15° C. When addition was complete, the mixture was stirred at room temperature for 2 hours, and the white solid was filtered off and washed with 100 mL of ether. The combined filtrates were reduced in volume to about 200 mL at reduced pressure and cooled in a refrigerator at about 5° C. overnight. The small amount of white solid that had separated was removed by filtration, and the solvents were evaporated at reduced pressure. The residue was taken up in 300 mL of ether, filtered, and the solvent evaporated to leave the title compound (61.5 g, 98%) with IR and NMR spectra consistent with the desired product.

Workup

  1. additionWhen addition
  2. filtrationthe white solid was filtered off
  3. washwashed with 100 mL of ether
  4. temperaturecooled in a refrigerator at about 5° C. overnight
  5. customThe small amount of white solid that had separated
  6. customwas removed by filtration
  7. customthe solvents were evaporated at reduced pressure
  8. filtrationfiltered
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-53082da8e2a741c39a9886777aa4f102
Source dataset
uspto-grants-2007_11
Patent number
US07294742B2

Reaction notes

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