Hydrochloric Acid → 3-[4-Cyanobenzyl]aminopropanoic acid

HRID 726719Notes

Reaction equation

HRID 726719 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].C([O:13][C:14](=[O:18])[CH2:15][CH2:16][NH2:17])C.Cl.C([BH3-])#N.[Na+].[OH-].[Li+].CO>CN(C)C=O.C(O)(=O)C>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:17][CH2:16][CH2:15][C:14]([OH:18])=[O:13])=[CH:5][CH:4]=1)#[N:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 660424-CyanobenzaldehydeHCID 419889Ethyl 3-aminopropanoateHCID 5003444Sodium cyanoborohydrideHCID 23717829Lithium hydroxide methanol

Product 1

HCID 167699873-[4-Cyanobenzyl]aminopropanoic acidYield 79%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

4-cyanobenzaldehyde (0.65 g; 5 mmoles) and β-alanine ethyl ester.HCl (0.76 g; 5 mmoles) were dissolved in N,N-dimethylformamide (10 ml) containing 1% acetic acid. After 10 min., sodiumcyanoborohydride (0.35 g; 5 mmoles) was added to the solution. The reaction mixture was stirred at room temperature for 12 hrs. and taken down to dryness under reduced pressure. The residue was treated with 1N lithium hydroxide/methanol (1:1; 20 ml) for 15 min. Methanol was removed and the pH of the remaining solution was adjusted to pH 5 with 50% acetic acid. The product was purified by HPLC using a linear gradient of acetonitrile/water/trifluoroacetic acid. The desired fractions was collected and lyophilized to give 0.81 g of white solid (79% yield). FAB-MS: MH+ =205.1.

Workup

  1. customMethanol was removed
  2. customThe product was purified by HPLC
  3. customThe desired fractions was collected

Sources & evidence

ORD record
ord-c6ad0981756643088329bfd4623ad976
Source dataset
uspto-grants-1998_01
Patent number
US05710166

Reaction notes

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