Ethyl 3-(methylamino)propanoate → HCID 68516611, compound

HRID 1877201Notes

Reaction equation

HRID 1877201 reaction equation
[CH3:1][CH:2]([CH3:31])[CH2:3][CH:4]([C:15]1[S:16][C:17]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)=[CH:18][C:19]=1[CH3:20])OC1C=CC(C(O)=O)=CC=1.CNC[CH2:35][C:36]([O:38]CC)=[O:37].Cl.C(N=C=N[CH2:47][CH2:48][CH2:49][N:50]([CH3:52])[CH3:51])C.[OH2:53].OC1[C:63]2N=N[NH:60][C:59]=2[CH:58]=[CH:57]C=1>CN(C)C=O.C(OCC)(=O)C>[CH3:52][N:50]([C:49]([C:48]1[CH:47]=[CH:63][C:59]([NH:60][CH:4]([C:15]2[S:16][C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:30])[F:29])=[CH:23][CH:22]=3)=[CH:18][C:19]=2[CH3:20])[CH2:3][CH:2]([CH3:1])[CH3:31])=[CH:58][CH:57]=1)=[O:53])[CH2:51][CH2:35][C:36]([OH:38])=[O:37]

Participants

7

Reactant 4

HCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68511264HCID 68511264, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 68516611HCID 68516611, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(3-methyl-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-2-yl}butoxy)benzoic acid (179 mg), ethyl 3-(methylamino)propanoate (63 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (92 mg), hydroxybenzotriazole monohydrate (74 mg) 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 1N hydrochloric acid, 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 sodium hydroxide (1.0 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (165 mg, 78%) as an amorphous compound.

Workup

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and 1N hydrochloric acid
  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 sodium hydroxide (1.0 mL)
  7. additionThe reaction mixture was poured into water
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-54f4581929c040528e6acf98d7f7333a
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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