Chloroacetyl chloride → HCID 40719601, compound

HRID 1611612Notes

Reaction equation

HRID 1611612 reaction equation
[NH2:1][C@H:2]([CH2:7][OH:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].C(N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19]>C(Cl)Cl>[Cl:16][CH2:17][C:18]([NH:1][C@H:2]([CH2:7][OH:8])[C@H:3]([CH2:5][CH3:6])[CH3:4])=[O:19]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 272402724629-25-2

Product 1

HCID 40719601HCID 40719601, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of L-isoleucinol (20 g, 0.17 mol) and triethylamine (28.56 ml, 0.204 mol) in CH2Cl2 (500 ml) at −78° C. was added chloroacetyl chloride (16.3 ml, 0.204 mol) over 5 minutes. The cooling bath was removed and the solution allowed to warm to −20° C. _The mixture was diluted with EtOAc and washed sequentially with 1 M HCl, and brine and dried (Na2SO4). Evaporation in vacuo afforded the amide title compound (35 g, 100%).

Workup

  1. customThe cooling bath was removed
  2. additionwas diluted with EtOAc
  3. washwashed sequentially with 1 M HCl, and brine
  4. dry with materialdried (Na2SO4)
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-f55da9c63cf144ffb1c3a77677d55ee0
Source dataset
uspto-grants-2006_01
Patent number
US06989383B1

Reaction notes

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