Triethylamine → N-(Cyclobutylcarbonyl)glycine ethyl ester

HRID 749170Notes

Reaction equation

HRID 749170 reaction equation
[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.[NH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C(N(CC)CC)C>ClCCl>[CH:1]1([C:5]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12176Glycine ethyl esterHCID 78705Cyclobutanecarbonyl chloride

Product 1

HCID 60810545N-(Cyclobutylcarbonyl)glycine ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclobutane carbonyl chloride (5 ml, 43.8 mmol) was slowly added to a solution of ethyl glycinate (5.86 g, 42 mmol) in dichloromethane (100 ml) and triethylamine (14.6 ml, 105 mmol) at 0° C. The mixture was then stirred at ambient temperature for 14 hours. The reaction mixture was washed with 1.0 N hydrochloric acid and the organic phase separated, dried (magnesium sulphate) and evaporated in vacuo to yield a yellow solid. Recrystallisation from dichloromethane:petroleum ether, yielded ethyl N-(cyclobutylcarbonyl)glycinate as a white solid (7.78 g, 100% yield):

Workup

  1. washThe reaction mixture was washed with 1.0 N hydrochloric acid
  2. customthe organic phase separated
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated in vacuo
  5. customto yield a yellow solid
  6. customRecrystallisation from dichloromethane

Sources & evidence

ORD record
ord-f953039aeb7a4d5cbf3971b41b371e97
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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