Acetic Acid → 3-(Dimethylamino)-2-(thiophen-3-yl)propanoic acid

HRID 409408Notes

Reaction equation

HRID 409408 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.CC(O)=O>C1COCC1.O.CO>[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

6

Reactant 4

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

Product 1

HCID 591617463-(Dimethylamino)-2-(thiophen-3-yl)propanoic acid

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-01a870b456d644579491227f767645d6
Source dataset
uspto-grants-2014_06
Patent number
US08759388B2

Reaction notes

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