Ethyl 3-(methylamino)propanoate → HCID 68512728, compound

HRID 1877063Notes

Reaction equation

HRID 1877063 reaction equation
[CH3:1][CH:2]([CH3:27])[CH2:3][CH:4]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)[C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][C:6]=1[CH3:16].[CH3:28][NH:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[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:22]([C:21]1[CH:20]=[CH:19][C:18]([NH:17][CH:4]([C:5]2[CH:9]=[C:8]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:7][C:6]=2[CH3:16])[CH2:3][CH:2]([CH3:1])[CH3:27])=[CH:26][CH:25]=1)=[O:24])[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

8

Reactant 4

HCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68514340HCID 68514340, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 68512728HCID 68512728, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-{[3-methyl-1-(2-methyl-5-phenylfuran-3-yl)butyl]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 give ethyl 3-{methyl[(4-{[3-methyl-1-(2-methyl-5-phenylfuran-3-yl)butyl]amino}phenyl)carbonyl]amino}propanoate. Ethyl 3-{methyl[(4-{[3-methyl-1-(2-methyl-5-phenylfuran-3-yl)butyl]amino}phenyl)carbonyl]amino}propanoate was dissolved in ethanol (2 mL) and tetrahydrofuran (2 mL) and 1N lithium hydroxide (1.0 mL) was added, 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 (186 mg, 83%).

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

Sources & evidence

ORD record
ord-ba5193cf72ae4619b4544e016e9a5edc
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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