(R)-2-(4-chloro-benzylamino)-3-methyl-butyric acid methyl ester → HCID 59834689, compound

HRID 271612Notes

Reaction equation

HRID 271612 reaction equation
CO[C:3](=[O:17])[C@H:4]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[CH:5]([CH3:7])[CH3:6].[O-:18][C:19]#[N:20].[K+]>C(O)(=O)C>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:8]2[C@H:4]([CH:5]([CH3:6])[CH3:7])[C:3](=[O:17])[NH:20][C:19]2=[O:18])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 8150601(R)-2-(4-chloro-benzylamino)-3-methyl-butyric acid methyl esterHCID 11378442Potassium cyanate

Product 1

HCID 59834689HCID 59834689, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1.68 g (6.59 mmoles) of (R)-2-(4-chloro-benzylamino)-3-methyl-butyric acid methyl ester in 20 ml of acetic acid, 0.64 g (7.91 mmoles) of potassium cyanate is added at ambient temperature under N2 atmosphere. The mixture is stirred for 15 hours at ambient temperature and heated for 3 hours at 100° C., and then the reaction mixture is concentrated under reduced pressure. The mixture is extracted with AcOEt, and the combined extracts are washed with sat. NaHCO3 and brine, dried over MgSO4 and then concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 1.57 g of desired (R)-1-(4-chloro-benzyl)-5-isopropyl-imidazolidine-2,4-dione in 77% yield.

Workup

  1. temperatureheated for 3 hours at 100° C.
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. extractionThe mixture is extracted with AcOEt
  4. washthe combined extracts are washed with sat. NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8d4fe44251374d84a781e4eb22e7633c
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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