Triethylamine → HCID 4674605, compound

HRID 2215251Notes

Reaction equation

HRID 2215251 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].CCN(CC)CC.[C:16](Cl)(=[O:20])[CH:17]([CH3:19])[CH3:18]>C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 4674605HCID 4674605, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10.00 g of glycine ethyl ester hydrochloride (71.6 mmol) and 21.97 ml of NEt3 (2.2 eq.) were dissolved in 200 ml of CH2Cl2 and treated between 0° and 5° dropwise with 7.81 ml of isobutyryl chloride (1.05 eq.), dissolved in 50 ml of CH2Cl2. The reaction mixture was allowed to reach ambient temperature (2.5 h) and then quenched by carefully pouring onto crashed ice/HCl/AcOEt. Separation of the layers, additional extraction of the aqueous phase with AcOEt, washing with Na2CO3 and brine, drying of the combined organic phase over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=6/4) yielded 11.74 g of the title compound as colorless oil.

Workup

  1. customto reach ambient temperature
  2. custom(2.5 h)
  3. customquenched
  4. additionby carefully pouring
  5. customSeparation of the layers, additional extraction of the aqueous phase with AcOEt
  6. washwashing with Na2CO3 and brine
  7. dry with materialdrying of the combined organic phase over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-698d1145e3f6427d8e6822914554faa6
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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