Triethylamine → HCID 22149514, compound

HRID 226198Notes

Reaction equation

HRID 226198 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, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To stirring mixture of 2-(2-chloro acetylamino)-2-methyl propionic acid (18.04 g, 0.10 mol), triethylamine (11.13 g, 0.11 mol), and 100 mL of acetone cooled with an ice bath was added ethyl chloroformate (10.52 mL, 0.11 mol) over 10 minutes. The reaction mixture was warmed to room temperature and 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 residue was distilled under reduced pressure (bp 59-60° C. at 7 mmHg) to give a colorless oil. A yield of 13.18 g (82%) was obtained.

Workup

  1. temperaturecooled with an ice bath
  2. stirringstirred for 2 hours
  3. filtrationThe mixture was then filtered
  4. concentrationthe filtrate was concentrated under vacuum
  5. additionHexane (200 mL) was added to the residue
  6. filtrationthe mixture was filtered
  7. customAfter removal of the solvent under vacuum
  8. distillationthe residue was distilled under reduced pressure (bp 59-60° C. at 7 mmHg)
  9. customto give a colorless oil
  10. customA yield of 13.18 g (82%) was obtained

Sources & evidence

ORD record
ord-2fff16649c624813bbf5de0e5e945bbc
Source dataset
uspto-grants-2009_07
Patent number
US07557177B2

Reaction notes

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