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

HRID 417500Notes

Reaction equation

HRID 417500 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>[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

8

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 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

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. additionwas added
  3. filtrationThe suspension was filtered
  4. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-6e5d2166ab8c49039fbcf28235bd4cbc
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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