Chloroacetyl chloride → HCID 40719601, compound

HRID 2293446Notes

Reaction equation

HRID 2293446 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 1M 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. additionThe mixture was diluted with EtOAc
  3. washwashed sequentially with 1M HCl, and brine
  4. dry with materialdried (Na2SO4)
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-b8d85f44d7d74c548da200735c31f637
Source dataset
uspto-grants-1997_11
Patent number
US05686472

Reaction notes

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