Ethyl 3-(methylamino)propanoate → HCID 59529467, compound

HRID 1877117Notes

Reaction equation

HRID 1877117 reaction equation
[CH:1]1([C:4]2[O:5][C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:7][C:8]=2[CH:9]([NH:14][C:15]2[CH:23]=[CH:22][C:18](C(O)=O)=[CH:17][CH:16]=2)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:3][CH2:2]1.[CH3:30][NH:31][CH2:32][CH2:33][C:34]([O:36]CC)=[O:35].Cl.C(N=C=NCCCN(C)C)C.O.[OH:52][C:53]1C2N=NNC=2C=CC=1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH:1]1([C:4]2[O:5][C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:7][C:8]=2[CH:9]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:53]([N:31]([CH3:30])[CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[O:52])=[CH:22][CH:23]=2)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68516778HCID 68516778, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 59529467HCID 59529467, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-{[1-(2-cyclopropyl-5-phenylfuran-3-yl)-3-methylbutyl]amino}benzoic acid (264 mg), ethyl 3-(methylamino)propanoate (108 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (157 mg), hydroxybenzotriazole monohydrate (126 mg) and triethylamine (114 μL) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 4 hr. Ethyl acetate was added, the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and water, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure. To the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (1.0 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (10 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (153 mg, 48%).

Workup

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and water
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionTo the residue were added ethanol (2 mL), tetrahydrofuran (2 mL) and 1N lithium hydroxide (1.0 mL)
  7. customThe solvent was evaporated under reduced pressure, and water (10 mL)
  8. additionwas added
  9. temperaturecooling
  10. stirringstirred for 1 hr
  11. filtrationThe resulting precipitate was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-442d81faf5774ab79ec4669070db65bd
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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