Glycine → N-[4-(2-Cyclopropylethoxy)benzoyl]glycine

HRID 1799228Notes

Reaction equation

HRID 1799228 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]1([CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.[NH2:22][CH2:23][C:24]([OH:26])=[O:25].C(N(CC)CC)C>CN(C)C=O.C1COCC1.C(Cl)Cl>[CH:7]1([CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:19])=[CH:20][CH:21]=2)[CH2:8][CH2:9]1

Participants

8

Reactant 4

HCID 750GlycineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 581116264-(2-Cyclopropylethoxy)benzoic acid

Product 1

HCID 66812105N-[4-(2-Cyclopropylethoxy)benzoyl]glycineYield 97%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (8.64 mL, 99.0 mmol) and one drop of N,N-dimethylformamide (DMF) were added to a methylene chloride (30 mL) solution of 4-(2-cyclopropylethoxy)benzoic acid (9.28 g, 45.0 mmol) prepared in Example 1 (1a), under ice-cooling. The mixture was stirred at room temperature for 1.75 hours, and then the solvent was evaporated. Then, the obtained residue was suspended in THF (3 mL). This suspension was dropwise added to a 50% THF aqueous solution (120 mL) of glycine (4.41 g, 58.7 mmol) and triethylamine (15.7 mL, 112 mmol) under ice-cooling. The resulting mixture was stirred at room temperature for 1.5 hours, and the solvents (mainly THF) were evaporated. Then, 10% hydrochloric acid (40 mL) was added to the residue under ice-cooling. The resulting precipitate was collected by filtration, washed with water, and dried by heating under reduced pressure to give 11.4 g of the title compound (powder, yield: 97%).

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated
  3. temperaturecooling
  4. stirringThe resulting mixture was stirred at room temperature for 1.5 hours
  5. customthe solvents (mainly THF) were evaporated
  6. additionThen, 10% hydrochloric acid (40 mL) was added to the residue under ice-
  7. temperaturecooling
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with water
  10. customdried
  11. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-d9cb177c13774476846005a0da467c5e
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

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