Hydrochloric Acid → 1-Benzyl-imidazolidine-4-carboxylic acid methyl ester

HRID 71794Notes

Reaction equation

HRID 71794 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([NH:14][C:15](OC(C)(C)C)=O)[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.C=O.S([O-])([O-])(=O)=O.[Mg+2].C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]([CH:4]1[CH2:5][N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:15][NH:14]1)=[O:22]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21609903HCID 21609903, compound

Product 1

HCID 666200461-Benzyl-imidazolidine-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

3-Benzylamino-2-tert-butoxycarbonylamino-propionic acid methyl ester (4.01 g, 13.02 mmol) was dissolved in dichloromethane (20 mL) and HCl (4M Dioxane, 40 mL) was added. The resultant suspension was stirred at room temperature for 30 minutes, after which all volatiles were removed in vacuo. The crude material was mixed with para-formaldehyde (390 mg, 13.02 mmol), magnesium sulfate (2.6 g), potassium carbonate (2.6 g) and suspended in chloroform (40 mL). Triethylamine (5.07 mL) was added and the reaction was stirred at room temperature for 48 hours. The suspension was filtered and the volatiles were removed in vacuo. The crude material 1-Benzyl-imidazolidine-4-carboxylic acid methyl ester (3.5 g) was used in the next step without further analysis.

Workup

  1. customafter which all volatiles were removed in vacuo
  2. filtrationThe suspension was filtered
  3. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-d9dcb9dcdcac407fbf35b70710d9f9d4
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

Loading…