Triethylamine → N-(3-Chlorobenzoyl)glycine ethyl ester

HRID 2276762Notes

Reaction equation

HRID 2276762 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].Cl.[NH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)CC)C>ClCCl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 2227495N-(3-Chlorobenzoyl)glycine ethyl esterYield 69.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 3-chlorobenzoyl chloride (6.0 mL, 58 mmol) in dichloromethane (150 mL) were added ethyl glycinate hydrochloride (10 g, 72 mmol) and triethylamine (20 mL, 142 mmol). After stirring for 1 h, the mixture was diluted with saturated NaHCO3 and the aqueous layer extracted twice with dichloromethane. The combined organic layers were dried over Na2SO4 and evaporated to dryness in vacuo to give the desired product (9.8 g) as a white solid which was taken on without purification.

Workup

  1. extractionthe aqueous layer extracted twice with dichloromethane
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-0355b144a9ec4e1cb86fc8e932801d3e
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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