Triethylamine → HCID 22149514, compound

HRID 1883908Notes

Reaction equation

HRID 1883908 reaction equation
[Cl:1][CH2:2][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>[Cl:1][CH2:2][C:3]1[O:8][C:7](=[O:9])[C:6]([CH3:11])([CH3:10])[N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 17605750N-(Chloroacetyl)-2-methylalanine

Product 1

HCID 22149514HCID 22149514, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirring mixture of 2-(2-chloro-acetylamino)-2-methyl propionic acid (18.0 g; 0.10 mol), triethylamine (11.1 g; 0.11 mol) and 100 mL acetone, cooled with an ice bath, was added ethyl chloroformate (10.5 mL; 0.11 mol) 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 filtrate was concentrated under vacuum. Hexane (200 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 (59-60° C.; 7 mmHg) to give 13.2 g (82%) of a colorless oil.

Workup

  1. temperaturecooled with an ice bath
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. additionHexane (200 mL) was added to the residue
  5. filtrationthe mixture was filtered
  6. customAfter removal of the solvent under vacuum
  7. distillationthe filtrate residue was distilled under reduced pressure (59-60° C.; 7 mmHg)

Sources & evidence

ORD record
ord-d08b7d73fc334a54b14b8f64db11f851
Source dataset
uspto-grants-2004_07
Patent number
US06762257B1

Reaction notes

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