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

HRID 456276Notes

Reaction equation

HRID 456276 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.Cl>CN(C=O)C.ClCCl>[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 5

HCID 313Hydrochloric AcidHCID 750GlycineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 581116264-(2-Cyclopropylethoxy)benzoic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (8.64 mL, 99.0 mmol) and one drop of DMF were added to a solution of dichloromethane (30 mL) containing 4-(2-cyclopropylethoxy)benzoic acid (9.28 g, 45.0 mmol) prepared in Example 9 (9a) under ice-cooling. The mixture was stirred at room temperature for 1.75 hours, and the solvent was evaporated. Then, the resulting residue was suspended in THF (3 mL). This suspension added dropwise to a 50% THF aqueous solution (120 mL) containing glycine (4.41 g, 58.7 mmol) and triethylamine (15.7 mL, 112 mmol) under ice-cooling. The mixture was stirred at room temperature for 1.5 hours, and then 10% hydrochloric acid (40 mL) was added thereto under ice-cooling. The produced 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. additionThis suspension added dropwise to a 50% THF aqueous solution (120 mL)
  4. temperaturecooling
  5. stirringThe mixture was stirred at room temperature for 1.5 hours
  6. temperatureunder ice-cooling
  7. filtrationThe produced precipitate was collected by filtration
  8. washwashed with water
  9. customdried
  10. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-cd52ca92ca1242c7a9ce456e8263b6ee
Source dataset
uspto-grants-2013_07
Patent number
US08497397B2

Reaction notes

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