Tetrahydrofuran → (2S)-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxo-1-imidazolidinyl}butanoic Acid

HRID 243595Notes

Reaction equation

HRID 243595 reaction equation
[CH3:1][CH:2]([CH3:19])[C@H:3]([NH:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]1[N:14]=[C:15]([CH3:18])[S:16][CH:17]=1)[C:4]([O:6]C)=[O:5].[O:20]1CCC[CH2:21]1>>[CH3:1][CH:2]([CH3:19])[C@H:3]([N:8]1[CH2:9][CH2:10][N:11]([CH2:12][C:13]2[N:14]=[C:15]([CH3:18])[S:16][CH:17]=2)[C:21]1=[O:20])[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 86598720methyl(2S)-3-methyl-2-[(2-{[(2-methyl-1,3-thiazol-4-yl)methyl]amino}ethyl)amino]butanoate

Product 1

HCID 66889014(2S)-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxo-1-imidazolidinyl}butanoic Acid

Procedure

A solution of the product of Example 143C (5.4 g) in tetrahydrofuran (80 mL) was treated with carbonydiimidazole (6.1 g, 2 equivalents) at 25° C. for 2 hrs. The mixture was quenched with 10% citric acid, the organic layer was separated, washed with water, brine, dried over Na2SO4, filtered, and the solvents were evaporated A solution of the residue (3.3 g) in dioxane (20 mL) was treated with 1M LiOH (20 mL) at 25° C. for 2 hrs. The solvents were evaporated, and the residue was acidified with 10% HCl, extracted with dichloromethane/2-propanol (3:1), the organic layer was separated, dried over Na2SO4, filtered, and the solvents evaporated to give 1.5 g of the title compound.

Workup

  1. customThe mixture was quenched with 10% citric acid
  2. customthe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were evaporated A solution of the residue (3.3 g) in dioxane (20 mL)
  7. additionwas treated with 1M LiOH (20 mL) at 25° C. for 2 hrs
  8. customThe solvents were evaporated
  9. extractionextracted with dichloromethane/2-propanol (3:1)
  10. customthe organic layer was separated
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. customthe solvents evaporated

Sources & evidence

ORD record
ord-529b474ccda14a9680f5789834868d48
Source dataset
uspto-grants-2014_02
Patent number
US08653141B2

Reaction notes

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