Ethyl 3-(methylamino)propanoate → HCID 59529370, compound

HRID 1877069Notes

Reaction equation

HRID 1877069 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:5][C:6]=1[CH:7]([NH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1)[CH2:8][CH2:9][CH2:10][CH3:11].[CH3:28][NH:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33].Cl.C(N=C=NCCCN(C)C)C.O.OC1C2N=NNC=2C=CC=1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:28][N:29]([C:17]([C:16]1[CH:20]=[CH:21][C:13]([NH:12][CH:7]([C:6]2[CH:5]=[C:4]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:3][C:2]=2[CH3:1])[CH2:8][CH2:9][CH2:10][CH3:11])=[CH:14][CH:15]=1)=[O:19])[CH2:30][CH2:31][C:32]([OH:34])=[O:33]

Participants

8

Reactant 4

HCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68512509HCID 68512509, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 59529370HCID 59529370, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-{[1-(2-methyl-5-phenylfuran-3-yl)pentyl]amino}benzoic acid (182 mg), ethyl 3-(methylamino)propanoate (79 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (115 mg), hydroxybenzotriazole monohydrate (92 mg) and triethylamine (84 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 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 (211 mg, 94%).

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 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-ec20d9b089224305a73697578d1c469c
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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