2-Thiophenecarboxaldehyde → Methyl 3-amino-3-(2-thienyl)propanoate

HRID 378136Notes

Reaction equation

HRID 378136 reaction equation
[NH2:1][CH:2]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][C:4]([OH:6])=[O:5].S1C=CC=[C:13]1C=O.Cl.O1CCOCC1.CCOCC.CC#N>CO>[NH2:1][CH:2]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][C:4]([O:6][CH3:13])=[O:5]

Participants

6

Reactant 4

HCID 73642-ThiophenecarboxaldehydeHCID 2493063-Amino-3-(thiophen-2-yl)propanoic acidHCID 204431481,4-Dioxane hydrochlorideHCID 21885917Acetonitrile ether

Product 1

HCID 2764295Methyl 3-amino-3-(2-thienyl)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-amino-3-(2-thienyl)propanoic acid (0.5 g) [prepared substituting a molar equivalent amount of 2-thiophene-carboxaldehyde in Example 57, Step A] in methanol (50 ml) was treated with 4N HCl/dioxane (10 ml). After 6 hours the excess solvent was removed under reduced pressure to give a waxy solid. Treatment with Et2O/CH3CN produced methyl β-aminothiophene-2-propanoate (370 mg) as a white powder. MS and 1H-NMR were consistent with the desired product.

Workup

  1. customAfter 6 hours the excess solvent was removed under reduced pressure
  2. customto give a waxy solid

Sources & evidence

ORD record
ord-2d23fc5e8f0b4601948e7527f629a05a
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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