Acetic Acid → NH3 MeOH EtOH

HRID 1690255Notes

Reaction equation

HRID 1690255 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH:4]([C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)[C:5]([O:7]C)=[O:6].[Li+].[OH-].O.[CH3:18][C:19](O)=[O:20]>C1COCC1.O.CO>[NH3:2].[CH3:5][OH:6].[CH3:18][CH2:19][OH:20].[CH3:14][N:2]([CH3:1])[CH2:3][CH:4]([C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 59161743Methyl 3-(dimethylamino)-2-(thiophen-3-yl)propanoate

Product 2

HCID 591617463-(Dimethylamino)-2-(thiophen-3-yl)propanoic acidHCID 86638423NH3 MeOH EtOHYield 10%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To methyl 3-(dimethylamino)-2-(thiophen-3-yl)propanoate (E42) in THF/H2O/MeOH was added LiOH*H2O, and the solution was stirred for 12 hours. AcOH was added and the solvents were evaporated. Column chromatography (SiO2, 10-15% 2M NH3-MeOH/EtOH) gave pure 3-(dimethylamino)-2-(thiophen-3-yl)propanoic acid (E43).

Workup

  1. customthe solvents were evaporated

Sources & evidence

ORD record
ord-58b4bc0e79224096bbf3fb9949783f68
Source dataset
uspto-grants-2012_04
Patent number
US08153656B2

Reaction notes

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