Benzoyl chloride → HCID 3622015, compound

HRID 2215213Notes

Reaction equation

HRID 2215213 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[CH3:9]CN(CC)CC.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=CC=C[CH:18]=1>C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:16](=[O:23])[C:17]([CH3:9])([CH3:22])[CH3:18])[CH3:3]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 3622015HCID 3622015, 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 210 ml of CH2Cl2 and treated between 0° and 5° dropwise with 9.256 ml of benzoyl chloride (1.05 eq.), dissolved in 30 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 sodium sulfate, and evaporation of the solvents left finally 13.06 g of pure title compound as colorless liquid.

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 sodium sulfate, and evaporation of the solvents
  8. waitleft finally 13.06 g of pure title compound as colorless liquid

Sources & evidence

ORD record
ord-550bd80a958642f28d4e6447a1988890
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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